Unexpected conversions of selected heteroorganic compounds
作者:J�zef Drabowicz
DOI:10.1002/hc.10077
日期:——
A few unexpectedconversions of selectedheteroorganiccompounds are described, including the formation of N-sulfonyl sulfenamide derivatives and the mixed phosphinyl-sulfenyl anhydrides in the reactions of sulfinyl chlorides with α-phenylethylamine or t-butyl-phenylphosphine oxide, respectively. Unexpected reactions of the ortho hydroxyalkyl-substituted diaryl sulfoxides and hypervalent sulfur and
bis-thiophosphoryl disulfides under kinetic resolution conditions (2:1 ratio) afforded enantiomerically enriched tertiary phosphine oxides or phosphine sulfides with ee values up to 39%. In a similar way from racemic tert-butylphenylchlorophosphine, opticallyactive tert-butylphenylphosphinoyl chloride with 50% ee was obtained. The same reaction performed under dynamic kinetic resolution conditions (1:1 ratio
Enantiomerically pure disulfides were reacted with various chiral P-III-derivatives with stereogenic phosphorus such as tertiary phosphines, halogenophosphines, phosphinite and phosphole under kinetic resolution conditions to afford enantiomerically enriched phosphine oxides or sulfides with ee values up to 50%. Enantiomeric excess rose to 70% under dynamic kinetic resolution-conditions in the case of tert-butylphenylchlorophosphine. (C) 2004 Elsevier Ltd. All rights reserved.
KRAWIECKA B.; MICHALSKI J.; WOJNA-TADEUSIAK E., J. ORG. CHEM., 51,(1986) N 22, 4201-4208