Journal of Organic Chemistry p. 663 - 669 (1991)
Update date:2022-08-03
Topics:
Russell, Glen A.
Yao, Ching-Fa
Tashtoush, Hasan I.
Russell, June E.
Dedolph, Douglas F.
Reaction of excess RS- (R=Ph, t-Bu) with Ph2C=C(SPh)NO2 in Me2SO form Ph2C=CHSR via conversion of the initial Michael-type adducts into Ph2C(SR)CH=NO2- and Ph2C=CHNO2.In a similar fashion, reaction of (EtO)2PO- with Ph2C=C(SPh)NO2 forms initially mainly PhSP(O)(OEt)2 and Ph2C
CH=NO2-, which upon acidic workup will yield the nitroalkane or the Nef reaction product, Ph2C
CHO.The reaction of (EtO)2PO- with Ph2C=C(SPh)NO2 also produces Ph2C
CN via a Perkow-type reaction of the Michael adduct to yield Ph2C
CH=N(O)OP(O)(OEt)2 as an intermediate.The nitrile is also formed from Ph2C
CH(NO2)2 with (EtO)2PO- in (EtO)2P(O)H or Me2SO at 30 deg C and in >95percent yield by the reaction of (EtO)3P with Ph2C
CH(NO2)2 at 150 deg C.Reaction of Ph2C=CHNO2 or Ph2C
CH2NO2 with excess (EtO)PO- in Me2SO or (EtO)2P(O)H forms 3-(diethoxyphosphinyl)-2,2-diphenylaziridine by a process postulated to involve Ph2C=CHN(O-)OP(O)(OEt)2, Ph2C=CHNOP(O)(OEt)2-, and 2,2-diphenyl-2H-azirine.Similarly, Ph2C=C(SBu-t)NO2 and (EtO)2PO- give 3-(tert-butylthio)-2,2-diphenyl-2H-azirine in Me2SO or 2-(tert-butylthio)-3-phenylindole in (EtO)2P(O)H solution.Deoxygenation of Ph2C=C(X)NO2 to form the 2-X-3-phenylindoles occurs in high yield at 150 deg C in (EtO)3P with X=H, PhS, or t-BuS while 2-nitrro-3-phenylindole is formed from Ph2C=C(NO2)2 in (EtO)2P(O)H at 150 deg C.
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