Publications

1964

Journal Articles

Advanced Problems and Solutions: Problems for Solution: 5161-5170

S. Warner; W. E. Briggs; S. D. Chatterji; G. Thompson; P. Truenfels et al. 

American mathematical monthly. 1964. Vol. 71, num. 1, p. 98-99. DOI : 10.2307/2311331.

Problems and Solutions: Solutions of Advanced Problems: 5159

S. D. Chatterji; D. Nixon; J. Wahab 

American mathematical monthly. 1964. Vol. 71, num. 10, p. 1143. DOI : 10.2307/2311433.

Problems and Solutions: Solutions of Advanced Problems: 5158

S. D. Chatterji; R. Laatsch 

American mathematical monthly. 1964. Vol. 71, num. 10, p. 1142-1143. DOI : 10.2307/2311432.

Certain induced measures on the unit interval

S. D. Chatterji 

Journal of the London Mathematical Society. 1964. Vol. 38, p. 325-331. DOI : 10.1112/jlms/s1-38.1.325.

Certain induced measures and the fractional dimensions of their ‘supports’

S. D. Chatterji 

Zeitschrift für Wahrscheinlichkeitstheorie und verwandte Gebiete*. 1964. Vol. 3, p. 184-192. DOI : 10.1007/BF00534907.

A note on the convergence of Banach-space valued martingales

S. D. Chatterji 

Mathematische Annalen. 1964. Vol. 153, p. 142-149. DOI : 10.1007/BF01361182.

Wideband high voltage probe

R. Keller 

Review of Scientific Instruments. 1964. Vol. 35, p. 1057. DOI : 10.1063/1.1718924.

High power RF pulse generator

E. Weibel 

Review of Scientific Instruments. 1964. Vol. 35, p. 173-175. DOI : 10.1063/1.1718772.

1963

Journal Articles

Contribution à l’étude du tracé d’aubage d’une turbine à réaction du type Francis

T. Bovet 

“Nous avons le plaisir de publier ici tout l’essentiel d’une conférence que notre Ingénieur-conseil, M. Th. Bovet, professeur de machines hydrauliques à l’E.P.U.L., a prononcée au Winter Meeting 1961 de l’A.S.M.E., à New-York.”

Informations Techniques Charmilles. 1963. Vol. 9, p. 47-70.

Advanced Problems and Solutions: Problems for Solution: 5151-5160

L. Ehrenpreis; J. D. Sondow; S. Kass; A. S. Davis; J. Hammer et al. 

American mathematical monthly. 1963. Vol. 70, num. 10, p. 1106-1108. DOI : 10.2307/2312857.

Some elementary characterization of the Poisson distribution

S. D. Chatterji 

American mathematical monthly. 1963. Vol. 70, p. 958-964. DOI : 10.2307/2313054.

Standardised description of crystal structures

D. Schwarzenbach 

Min. Petr. Mitt.. 1963. Vol. 43, p. 41-48. DOI : 10.5169/seals-33434.

Acid-catalyzed hydrolysis of diazo ketones. II. Acid-catalyzed H-D exchange

H. Dahn; A. Donzel; A. Merbach; H. Gold 

Helvetica Chimica Acta. 1963. Vol. 46, num. 6, p. 994-1000. DOI : 10.1002/hlca.19630460661.

1962

Journal Articles

Umlagerung und Abbau alpha-heterofunktionell substituierter Phosphoniumsalze

M. Schlosser 

Angewandte Chemie. 1962. Vol. 74, num. 8, p. 291. DOI : 10.1002/ange.19620740805.

Rearrangement and degradation of alpha-heterofunctional substituted phosphonium salts

M. Schlosser 

cf. CA 55, 23400c; Hellmann and Bader, CA 56, 11615h. Treatment of phosphonium salts of the type (Ph3PCH2X)OH(I, X = SMe; II, X = Cl; III, X = Br) with N aq. NaOH gave Ph3PO and MeX. With II and III a Ph group migrated to give Ph2(PhCH2)PO (17% from II, 33% from III). BuLi or PhLi also initiated this rearrangement in nonaq. solvents. The reaction is formulated II + RLi -> Ph3P:CHCl (IV); IV + RLi -> Ph3PRCHCl (V); V -> Ph2PR:CHPh (R = Bu, Ph, or OH). [on SciFinder (R)]

Angewandte Chemie, International Edition. 1962. Vol. 1, p. 266. DOI : 10.1002/anie.196202661.

Die Zersetzung von Diazoverbindungen in Gegenwart von Triphenylphosphin

G. Wittig; M. Schlosser 

cf. CA 55, 23400c. The Cu salt decompn. of diazo compds. in the presence of Ph3P opens up a new path to the synthesis of phosphorus-ylides. Ph3P (10 millimoles) and 10 millimoles 0.6M CH2N2 in Et2O treated 15 min. with 1 millimole anhyd. CuCl in 70 ml. tetrahydrofuran with vigorous evolution of N and the residue on evapn. hydrolyzed with dil. HCl, the soln. extd. to yield 6.5% Ph3PO, and the aq. phase neutralized with NaBPh4 yielded 13% [MePPh3]BPh4 (I), m. 195-6 Deg. In addn. 0,63 g. H2O- and Et2O-insol. adduct [Ph3P]2.CuCl (II), m. 239-42 Deg (Medoks and Andronova, CA 47, 9290g.) was isolated. Similar decompn. in Et2O gave 79% Ph3P, 13% Ph3PO, and 1.6% I. Decompn. in Et2O with addn. of 5 ml. C5H5N to the CuCl complex yielded 54% Ph3P,15% Ph3PO, and 2.6% I. Ph3P (10 millimoles) treated as above with 10 millimoles PhCHN2 in 20 ml. tetrahydrofuran 1 hr. to complete evolution of N, the red soln. decolorized with HCl, and the products isolated gave 10% PhCH2PPh3Cl, m. 325-8 Deg (PhCH2PPh3BPh4, m. 228-32 Deg), 10% Ph3P, 45% Ph3PO, and 41% PhCH:NN:CHPh. Ph3P (15 millimoles) and 1 millimole CuCl in 15 ml. boiling tetrahydrofuran treated dropwise in 90 min. with 15 millimoles Ph2CN2 in 15 ml. tetrahydrofuran, the mixt. refluxed 4 hrs. to complete evolution of N, and the mixt. hydrolyzed with acid yielded 34% Ph2CHPPh3Cl, m. 280-2 Deg. The Et2O-sol. portion contained 11% Ph3PO and 9% Phe(2HOH. An analogous reaction with 15 millimoles diazofluorene as diazo component yielded 32% 9-fluorenyl triphenylphosphonium bromide, m. 307-10 Deg, 14% fluorenone azine, m. 253-6 Deg, and 71% Ph3PO. Decompn. with 15 millimoles N2CHCO2Et as diazo component yielded 27% [EtO2CCH2PPh3]BPh4 (III), m. 173-5 Deg and 44% Ph3PO. The same reaction with 1 millimole AgNO3 as catalyst gave only 4% III and 67% Ph3PO. Use of 15 millimoles N2CHCOPh and direct treatment of the mixt. with petr. ether, followed by fractional crystn. from C6H6-petr. ether yielded 28% stable Ph3P:CHCOPh, m. 180-2 Deg, together with 5% Ph3P and some Ph3PO. Ph3P:CHPh (25 millimoles prepd. from 9.7 g. PhCH2PPh3Cl and 28 ml. 0.9M PhLi in 50 ml. tetrahydrofuran) decolorized by stirring 2 days (N atm.) with 25 millimoles PhCHN2 in 10 ml. tetrahydrofuran, the decoloration completed by addn. of alc.-Et2O and the mixt. filtered, the unchanged starting material converted into 22% [PhCH2PPh3]BPh4, m. 228-32 Deg, and the filtrate treated with 10 ml. MeI yielded 4.26 g. ppt., purified to give 31% MePPh3I, m. 188-9 Deg. The Et2O-sol. material chromatographed yielded 40% PhCH:NN:CHPh, resin, and small amts. of BzH and Ph3PO. Ph3P (20 millimoles) and 20 millimoles Ph2CO stirred in 70 ml. tetrahydrofuran with 1 millimole CuCl and treated in 1 hr. dropwise with 22 millimoles CH2N2 in Et2O, the tetrahydrofuran evapd. and the residue hydrolyzed, extd. with Et2O and the ext. treated with MeI to remove 18% Ph3P as Ph3PMeI, the Et2O evapd. from 45% Ph3PO and the fraction, b14 142-72 Deg, chromatographed over neutral Al2O3 yielded 23% Ph2C:CH2 and 67% Ph2CO. The CH2N2 replaced by an equimolar amt. of PhCHN2 in 20 ml. tetrahydrofuran and the mixt. refluxed 50 hrs. yielded 23% Ph2C:CHPh, m. 69-71 Deg; 6% trans-stilbene, 34% PhCH:NN:CHPh, 52% Ph2CO, and 33% Ph3PO. With BzH as carbonyl component, PhCHN2 was again added dropwise in 1 hr. to the boiling mixt. and the mixt. refluxed 1 hr. The Et2O-sol. product consisted of 28% cis- and trans-stilbene, 71% PhCH:NN:CHPh and 89% Ph3PO. Ph2P:NN:CH2[10 millimoles, m. 143-5 Deg (decompn.)] and 10 millimoles Ph2CO refluxed 4 hrs. with 1 millimole CuCl in 20 ml. MeOCH2CH2OMe and the filtered soln. dild. with Et2O, treated with MeI, and filtered gave 0.492 g. MePPh3I (corresponding to 12% Ph3P). The filtrate distd. and the bright yellow oil, b14 128-75 Deg, sepd. by column chromatography gave 35% Ph2C:CH2 and 52% Ph2CO. The distn. residue contained 72% Ph3PO. Repetition with 3-fold molar amt. of Ph2P:NN:CH2 and 4 hrs. reflux yielded 32% unchanged material, 51% Ph3PO, 31% unchanged Ph2CO, and 62% Ph2C:CH2. Diazofluorene (20 millimoles) in 15 ml. tetrahydrofuran added dropwise in 15 min. with stirring to 20 millimoles PhCH2NMe2 and 0.5 millimole CuCl with violent evolution of N (exothermic reaction) and the mixt. refluxed briefly, the cooled mixt. dild. with 100 ml. Et2O and washed with dil. HCl, the Et2O ext. dried and evapd. yielded 65% fluorenylenefluorene, m. 189-90 Deg. The acid ext. neutralized, extd. with Et2O and the product distd. gave 60% unchanged PhCH2NMe2. The distn. residue recrystd. from MeOH yielded 12% (9-benzyl-9-fluorenyl))dimethylamine, m. 99-101 Deg. N2CHCO2Et (20 millimoles) similarly decompd. and the basic fraction extd. with Et2O and distd. gave 2.38 g. material, b14 65-150 Deg, contg. mainly PhCH2NMe2 and about 5% PhCH2CH(NMe2)CO2Et, isolated by preparative gas chromatography to yield 0.19 g. pure amine. [on SciFinder (R)]

Tetrahedron. 1962. Vol. 18, num. 9, p. 1023-1028. DOI : 10.1016/S0040-4020(01)99266-X.

1961

Journal Articles

Elektrische Quadrupolwechselwirkung von Al27 in AlPO4

E. Brun; P. Hartmann; F. Laves; D. Schwarzenbach 

Helvetica Physica Acta. 1961. Vol. 34, p. 388-391.

Abwandlung der Phosphylen-Methodik : über Phosphin-alkylene als olefinbildende Reagenzien

G. Wittig; H. D. Weigmann; M. Schlosser 

cf. CA 50, 10030g. The stationary ligands on the P were varied in order to obtain an insight into the mechanism of the carbonyl-olefination with triphenylphosphylenes. The results demonstrated that the substitution of the Ph by p-MeC6H4, p-MeOC6H4, piperidino, and morpholino groups favored the betaine formation with carbonyl derivs., but rendered the decompn. reaction via the 4-ring markedly more difficult. (o-MeOC6H4)3P (I)(20 g.), m. 204-6 Deg, in 200 cc. Et2O and 20 g. MeBr kept 24 hrs. and the deposit boiled with C6H6 left 24 g. I.MeBr, m. 234-6 Deg (H2O). I.MeBr (10 millimoles) shaken 5 hrs. with 10 millimoles PhLi in 60 cc. Et2O, the mixt. treated with 10 millimoles BzPh in a small amt. of dry Et2O, shaken 15 hrs., heated 16 hrs. at 65 Deg, filtered, the residue extd. with C6H6, and treated with N HCl gave 81% I.MeBr; the C6H6 ext. concd. and dild. with petr. ether pptd. 10% (o-MeOC6H4)3PO (II), m. 215-17 Deg (subliming from 175 Deg). I (0.5 g.) in 20 cc. AcOH treated dropwise with excess 30% H2O2 and refluxed briefly gave II, m. 217-18 Deg (H2O). The original Et2O filtrate treated with dil. HCl, the mixt. evapd., and the residual oil chromatographed on Al2O3 yielded 11% Ph2C:CH2 (III), b16 150-60 Deg, and 58% unchanged BzPh. I.MeBr (5 millimoles) treated in the usual manner with 5 millimoles PhLi in Et2O, the ppt. suspended in dry Et2O, kept 14 days with 50 millimoles MeI, and the mixt. hydrolyzed with acid gave 69.5% I.EtI, m. 225-7 Deg (decompn.)(EtOH-Et2O). I (0.1 g.) and 1.5 g. EtI in 30 cc. Et2O kept 20 hrs. at 85 Deg yielded 86% I.EtI, m. 227-9 Deg (H2O). PCl3 (0.02 mole) in 50 cc. dry Et2O added dropwise with stirring during 0.5 hr. to 0.08 mole p-MeC6H4Li in 100 cc. Et2O and the mixt. decompd. after 24 hrs. with aq. NH4Cl gave 82% (p-MeC6H4)3P (IV), m. 145-6 Deg (EtOH). IV (18 g.) and 40 g. MeBr in 200 cc. C6H6 gave during 24 hrs. 96.5% IV.MeBr, m. 220.5-22 Deg (BuOH-Et2O). Powd. IV.MeBr (10 millimoles) and 10 millimoles PhLi in 60 cc. Et2O shaken 3 hrs., treated with 10 millimoles BzPh, the mixt. shaken 10 hrs., decompd. with 10 cc. N HCl, and filtered gave 81% (p-MeC6H4)3PO (V), m. 144-5 Deg (C6H6-petr. ether); the Et2O phase gave 69% III. (p-MeC5H43P:CH2 (VI) (5 millimoles) and 10 millimoles BzH heated 7 hrs. at 65 Deg gave 12% V, m. 143-4 Deg, and an oil which with Ph4BNa gave 61% [PhCH(OH)CH2(p-MeC6H4)3P]BPh4, m. 170-1 Deg; the original Et2O filtrate yielded 6% styrene. (p-MeOC6H4)2P (17 g.), m. 131-2 Deg, and 20 g. MeBr in 200 cc. Et2O gave during 24 hrs. 91% [(p-MeOC6H4)3PMe]Br (VII), m. 214-16 Deg (EtOH-Et2O). VII (10 millimoles) and 10 millimoles PhLi in 60 cc. Et2O shaken 20 hrs., treated with 10 millimoles BzPh in dry Et2O, the mixt. shaken 40 hrs., filtered, and the residue decompd. with HCl gave (p-MeOC6H4)3PO (VIII), m. 146-6.5 Deg (C6H6-petr. ether); the filtrate treated with N HCl and the Et2O phase worked up yielded addnl. VIII and 45% III; the aq. HCl phase neutralized and treated with KI yielded 15% iodide analog of VII, m. 218-20 Deg (H2O). VII treated in the usual manner with PhLi and then with BzPh gave 72% [(p-MeOC6H4)3PCH2CH(OH)Ph]BPh4, (IX), m. 211-13 Deg (decompn.) (BuOH). VII (10 millimoles) and 10 millimoles BzH heated 16 hrs. at 65 Deg and processed in the usual manner yielded 68% IX, m. 210-12 Deg (BuOH). (PhO)3P (X), b0.2 168-9 Deg, (10 millimoles) and 12 millimoles MeI in 5 cc. dry MeNO2 heated 3 hrs. in a sealed tube at 110-20 Deg, cooled, and dild. with dry Et2O pptd. X.MeI, m. 114-19 Deg (sealed capillary). X.MeI (6 millimoles) in 10 cc. dry Et2O treated dropwise with stirring with 6 millimoles Ph3Na in 58 cc. Et2O, the mixt. stirred 0.5 hr., treated with 6 millimoles BzPh, kept 2 days, heated 8 hrs. at 110 Deg, and worked up yielded 0.94 g. III. [Me3O]BF4 (28 millimoles) and 28 millimoles X stirred 5 hrs. at 65 Deg under N gave [MeP(OPh)3]BF4 (XI), m. 69 Deg (sealed capillary). XI, powd. PhOK, and BzPh (28 millimoles each) in 60 cc. dry tetrahydrofuran shaken 0.5 hr. under N, heated 18 hrs. at 140 Deg, filtered, and distd. gave 1.95 g. hOH, 1.0 g. III, and 2.5 g. unchanged BzPh; during the distn. 3.5 g. KBF4 sepd. from the mixt. Methyltripiperidinophosphonium iodide (XII), m. 254-5 Deg (decompn.), and PhLi (10 millimoles each) shaken 2 days in 32 cc. Et2O, decompd. with 150 cc. 0.1N HI, the aq. phase neutralized, and evapd. gave 3.1 g. unchanged XII; the Et2O phase treated with 10 millimoles BzPh in a little dry Et2O and the Et2O decanted gave a residue of the betaine, which treated with 0.3N HI yielded (2-hydroxy-2,2-diphenylethyl)tripiperidinophosphonium iodide (XIII). XIII heated at 70-80 Deg/0.05 mm. gave BzPh and XII. XIII (15 millimoles) in 50 abs. tetrahydrofuran shaken 12 hrs. with 15 millimoles PhLi in 16 cc. Et2O, treated with 15 millimoles BzPh, heated 36 hrs. at 110 Deg, and worked up gave 53% III and 3% BzPh. Trimorpholinophosphine (0.29 mole), m. 152-6 Deg, in 700 cc. 1:1 CH2Cl2-C6H6 treated dropwise at 0 Deg with 0.38 mole MeI, the mixt. kept 10 hrs. at room temp., and filtered gave 45% methyltrimorpholinophosphonium iodide (XIV), m. 328-30 Deg (decompn.) (aq. EtOH), which with NaBPh4 in hot MeOH gave the tetraphenylboronate, m. 239-40 Deg (Me2CO-EtOH). XIV and PhLi (12 millimoles each) in 50 cc. Et2O shaken 4 days and the ppt. treated with aq. HI gave 75% XIV. The trimorpholinophosphine-methylene from a similar run heated 41 hrs. at 70 Deg with an equiv. amt. of BzPh gave 88% unchanged BzPh, but no III. XIV and PhLi (36 millimoles each) in 90 cc. tetrahydrofuran stirred 10 min., treated with 36 millimoles BzPh, the mixt. heated 18 hrs. at 75 Deg, filtered, and the filtrate worked up gave 72% III, b14 132-6 Deg, and 12% BzPh. A similar run in dry (CH2OMe)2 heated 38 hrs. gave 80% III, 8% BzPh, and 33% trimorpholinophosphine oxide, m. 186-8 Deg (cyclohexane). A run with XIV and BzH in (CH2OMe)2 heated 20 hrs. at 65 Deg, filtered, and the residue treated with H2O yielded 49% 2-hydroxy-2-phenylethyl)trimorpholinophosphonium iodide, m. 268-70 Deg (MeOH-EtOH), stable on brief boiling with dil. HI; a soln. in hot MeOH gave with Ph4BNa the tetraphenylboronate, m. 272-4 Deg. [on SciFinder (R)]

Chemische Berichte. 1961. Vol. 94, num. 3, p. 676-689. DOI : 10.1002/cber.19610940316.

Über die Herstellung von Vinyläthern, Vinylthioäthern und Vinylhalogeniden auf der Phosphylen-Basis

G. Wittig; M. Schlosser 

cf. CA 55, 13345i. MeOCH2Ph3PCl (I), m. 201-2 Deg (decompn.) (CHCl3-AcOH), was prepd. (86%) from 0.19 mole Ph3P (II) and 0.2 mole ClCH2OMe in 120 ml. C6H6 (60 hrs. at 50 Deg); I borate analog m. 198-9 Deg (Me2CO-EtOH). Ph2CO (0.02 mole) dissolved in 40 ml. Et2O was added to a soln. resulting from the addn. of 0.02 mole PhLi in 20 ml. Et2O to a suspension of 0.02 mole I in 65 ml. Et2O. After 2 hrs., the ppt. was filtered off, washed with Et2O, and treated with dil. HCl and C6H6. MeOCH:CPh2 (III) (82%), m. 38-9 Deg (MeOH), was isolated by evapn. of the Et2O ext. and distn. III was converted to Ph2CHCHO (IV) by heating it 20 hrs. in 200 ml. AcOH-20 ml. H2SO4. BzH (0.7 mole) in 40 ml. tetrahydrofuran (THF) was added to a suspension of 0.1 mole I in 180 ml. THF (to which had been added 0.1 mole PhLi in 92 ml. Et2O). The ppt. was filtered off, the filtrate treated with a satd. soln. of NH4Cl, and the dried org. phase evapd. until 8.9 g. Ph3P(O) (V) crystd. Upon fractionation, the mother liquor yielded 61% PhCH:CHOMe (VI), b15 91-6 Deg. BuLi (0.12 mole) in 94 ml. Et2O was added to a stirred suspension of 0.12 mole I in 50 ml. Et2O at -50 Deg, the mixt. allowed to stand 2 hrs., and then 0.1 mole BzH added. After warming to room temp., the mixt. was kept 2 hrs., hydrolyzed with stirring, the Et2O phase successively washed with 40% NaHSO3, NaHCO3, and H2O, the Et2O removed, and the residue distd. to give a liquid, b14 90-9 Deg, contg. (vapor phase chromatography) 23% cis- and trans-VI, 11% PhCH:CHCH2CH2Me, 0.5% BzH, and PhCH2OH (trace). I (0.033 mole) was treated with 0.03 mole NaOEt in 70 ml. abs. EtOH; 0.03 mole BzH was added to the mixt., which was then warmed 5 hrs. at 65 Deg. EtOH was largely removed and the mother liquor fractionated to yield 0.0187 mole VI, which reacted with 5% H2SO4 to yield PhCH2CHO; 2,4-dinitrophenylhydrazone, m. 120-1 Deg. I (0.105 mole) was treated with 0.067 mole PhCH:CHCHO and 0.1 mole NaOEt in 200 ml. abs. EtOH 24 hrs. at 50 Deg and the mixt. worked up as before to yield 0.061 mole V and 50% MeOCH:CHCH:CHPh (VII), b0.1 74-5 Deg (over LiAlH4), n20D 1.6313. VII was characterized by reaction with maleic anhydride to yield 6-methoxy-3-phenyl-D4-tetrahydrophthalic anhydride, m. 166-7 Deg (C6H6). I was treated with 0.033 mole fluorenone and 0.05 mole NaOMe in 60 ml. abs. MeOH 53 hrs. at 50 Deg to yield 47% 9-(methoxymethylene)fluorene, m. 108-8.5 Deg; 1,3,5-(O2N)3C6H3 addn. product (1:1) m. 198-9 Deg (EtOH). 9-(Ethoxymethylene)fluorene was prepd. by a similar procedure using NaOEt and EtOH; 1,2,3-(O2N)3C6H3 addn. product (1:1) m. 166-7 Deg. I (0.094 mole) was kept 60 hrs. at 50 Deg with 0.033 mole phthalaldehyde and 0.088 mole NaOEt. V (80%) and Ph2P(O)CH2OMe (small amt.), m. 113.5-14 Deg (cyclohexane-AcOEt), were isolated as the Et2O-insol. portion of the residue. After the Et2O ext. was washed with NaHSO3, Na2CO3, and H2O, 55% 1,2-(MeOCH:CH)2C6H4, b0.8 102-3 Deg (over LiAlH4), was obtained by evapn. MeSCH2PPh3Cl (VIII), m. 220-2 Deg (CHCl3-AcOEt), was prepd. (77%) by heating 0.17 mole II and 0.2 mole MeSCH2Cl in 80 ml. C6H6 at 80 Deg with stirring. Treatment of VIII with NaPh4B yielded MeSCH2PPh3(BPh4), m. 210.5-11.0 Deg (MeCO-EtOH). PhLi (0.05 mole) in 46 ml. Et2O was added to 0.05 mole VIII in 100 ml. Et2O (15 min., with stirring) and the mixt. treated with 0.05 mole Ph2CO. The mixt. was agitated 40 hrs., dild. with Et2O, and treated with NH4Cl soln. to give 84% MeSCH:CPh2 (IX), m. 74.0-4.5 Deg (EtOH), from the Et2O layer. IX (0.005 mole) was boiled 20 hrs. in 20 ml. AcOH-20 ml. 10% H2SO4 soln. After neutralization, the soln. was extd. with Et2O, the Et2O evapd., and the residue crystd. from EtOH to yield 63% unchanged IX and 5% IV, isolated as its 2,4-dinitrophenylhydrazone, m. 148.5-9.5 Deg (EtOH). PhLi (0.074 mole) in 70 ml. Et2O was added with stirring to 0.075 mole VIII in 150 ml. THF and the mixt. stirred 15 min. after addn. BzH (0.067 mole) was then added (exothermic reaction) and heating continued 60 hrs. at 55 Deg. After filtration and in vacuo remov l of solvent, the residue was taken up in Et2O, the Et2O layer washed (H2O), the Et2O evapd., and petr. ether added to ppt. V. From the filtrate, 70% MeSCH:CHPh (X), b12 126-7 Deg, n20D 1.6334, was obtained by fractional distn. X was oxidized to a cis-trans mixt. of MeSO2CH:CHPh (XI), m. 50 Deg (petr. ether), with H2O2 in AcOH. cis-XI, m. 64 Deg (CHCl3), was isolated by fractional crystn. A mixt. of 0.021 mole X and 0.021 mole Me2SO4 was kept 60 hrs., dissolved in EtOH, and treated with a warm EtOH soln. of 0.025 mole NaPh4B to give Me3S(Ph4B), m. 328-30 Deg (Me2CO-EtOH). Me3O(BF4) (0.078 mole) in 60 ml. CH2Cl2 reacted with 0.08 mole X in 10 ml. CH2Cl2 to yield 73% Me2SCH:CHPh(BF4) (XII), m. 103-4 Deg (EtOH). Crude XII (0.025 mole) dissolved in 50 ml. Et2O was stirred with 0.05 mole PhLi in 47 ml. Et2O (exothermic reaction), the mixt. allowed to stand overnight, the soln. decanted and washed with H2O, the solvent removed, and the oil distd.; the fraction b760 34-90 Deg contained Me2S; the fraction b760 90-115 Deg contained PhC.tplbond.CH and X. trans-Stilbene was isolated from the residue. II (1 mole) and 1 mole paraformaldehyde (XIII) in 1 l. Et2O was stirred 10 hrs. with 500 ml. 33% HBF4; the ppt. was filtered off, washed with H2O, THF, and Et2O to yield 64% HOCH2PPh3(BF4) (XIV), m. 128-30 Deg (CH2Cl2AcOEt). II (2 moles) and 2 moles XIII in 1 l. Et2O was treated 3 hrs. with HCl to give HOCH2PPh3Cl (XV), m. 194-8 Deg (pptd. from CH2Cl2 with Et2O). XV was dissolved in 1.2 l. CH2Cl2 and heated 30 min. with 3 moles SOCl2, the volatile materials removed, the residue dissolved in warm CH2Cl2, and 440 g. ClCH2PPh3Cl (XVI), m. 260-1 Deg (CH2Cl2-AcOEt), pptd. with hot AcOEt. Equiv. amts. of XVI and NaBPh4 in EtOH yielded ClCH2PPh3(Ph4B), m. 222.0-3.8 Deg (Me2CO). XVI (0.115 mole) was refluxed with 0.110 mole NaOMe in 200 ml. MeOH under N; after 15 min., 0.1 mole BzH in 50 ml. MeOH was added. After being refluxed 15 min., the mixt. was treated with 5 g. NH4Cl and the solvent removed. The residue was extd. with boiling petr. ether, the exts. combined, concd., chromatographed on Al2O3LiBr, and eluted with 1 l. petr. Et2O to give 5.7 g. ClCH:CHPh (XVII), b13 81.5-2.5 Deg, n20D 1.5734. BuLi (0.12 mole) in THF was added dropwise to 0.115 mole XVI in 50 ml. THF; 0.1 mole BzH was added at -70 Deg and the mixt. warmed to 20 Deg and maintained 15 hrs. with stirring to give 35% XVII. When (MeOCH2)2 was used as the solvent, 67% XVII was obtained; when Et2O was used, 39% XVII was obtained. At 20 Deg, trans-1-phenyl-1-pentene, b12 109-9.5 Deg, n20D 1.5294, and a small amt. of the cis isomer were formed. BuLl (0.115 mole) in 90 ml. Et2O was added to 0.115 mole XVI in 50 ml. Et2O at -30 Deg; 0.1 mole Ph2CO was added at -30 Deg and the mixt. worked up as before (chromatography) to yield 67% Ph2C:CHCl (XVIII), b14 165-95 Deg, m. 42-3 Deg (MeOH). BuLi (0.04 mole) in 22 ml. Et2O was added dropwise to a soln. of 0.035 mole II in 45 ml. CH2Cl2 with stirring, 0.028 mole Ph2CO was added at -50 Deg, and after 3 days Et2O and H2O were added. II was pptd. as Ph3PMeI (by addn. of MeI) and the soln. concd. to give x-Ph2C(OH)C6H4P(O)Ph2. The mother liquor was chromatographed on Al2O3 to yield 1.88 g. XVIII. [on SciFinder (R)]

Chemische Berichte. 1961. Vol. 94, num. 5, p. 1373-1383. DOI : 10.1002/cber.19610940532.

1960

Journal Articles

Martingales of Banach-valued random variables

S. D. Chatterji 

Bulletin of the American Mathematical Society. 1960. Vol. 66, num. 5, p. 395-398. DOI : 10.1090/S0002-9904-1960-10471-5.

Triphenylphosphin-chlormethylen

G. Wittig; M. Schlosser 

cf. S., Dissertation, Heidelberg, 1960. The reaction of CH2Cl2 with BuLi and Ph3P yields Ph3P:CHCl, which reacts with Ph2CO to give 31% Ph2C:CHCl and Ph3PO. [on SciFinder (R)]

Angewandte Chemie. 1960. Vol. 72, num. 9, p. 324. DOI : 10.1002/ange.19600720913.

1959

Journal Articles

Electrical governors for hydraulic turbines. I. The Erelstat electric governor

A. Germond 

The development of the purely electric governor is summarized. Guiding design principles are enumerated, especially as regards the use of static apparatus and the absence of rubbing contacts. The action of the Erelstat electric governor, which is mainly electronic, is described in detail and practical results are given.

Revue générale de l’électricité. 1959. Vol. 68, num. 10, p. 565-570.

Evolution et état actuel de la construction des turbines hydrauliques

T. Bovet 

Bulletin technique de la suisse romande. 1959. Vol. 85, num. 4, p. 37-51. DOI : 10.5169/seals-64107.

1958

Journal Articles

Abrasive Erosion Phenomena in Hydraulic Turbines

T. Bovet 

The Engineers’ Digest. 1958. Vol. 19, num. 3, p. 107-110.

Contribution à l’étude du phénomène d’érosion par frottement dans le domaine des turbines hydrauliques

T. Bovet 

Bulletin technique de la Suisse romande. 1958. Vol. 84, num. 3, p. 37-49. DOI : 10.5169/seals-63478.