Thiophilic addition of organolithiums to aliphatic sulfines

被引：17

作者：

Alayrac, C ^{[1
]}

Cerreta, F ^{[1
]}

Chapron, I ^{[1
]}

Corbin, F ^{[1
]}

Metzner, P ^{[1
]}

机构：

[1] UNIV CAEN,ISMRA,CNRS,LAB CHIM MOL & THIO ORGAN,F-14050 CAEN,FRANCE

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 26期

关键词：

D O I：

10.1016/0040-4039(96)00869-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enethiolizable sulfines, freshly generated by oxidation of dithioesters, have been reacted with organolithiums. The reaction follows a selective thiophilic course leading to stabilised dithioacetal oxide carbanions, which have been subsequently treated with electrophiles. The resulting dithioacetal oxides are readily transformed into aldehydes or spontaneously to ketones. The specificity of this ''Umpolung'' related chemistry is that it involves an addition reaction and not a deprotonation. Carbophilic addition has not been evidenced and enethiolization appears very limited. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：4507 / 4510

页数：4

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