Facile [2,3]-rearrangements of difluoroallylic alcohols with C-P and C-S bond formation

被引：14
|
作者：
Blades, K [1 ]
Patel, ST [1 ]
Percy, JM [1 ]
Wilkes, RD [1 ]
机构：
[1] UNIV BIRMINGHAM,SCH CHEM,BIRMINGHAM B15 2TT,W MIDLANDS,ENGLAND
来源：
TETRAHEDRON LETTERS | 1996年 / 37卷 / 35期
基金：
英国工程与自然科学研究理事会;
关键词：
D O I：
10.1016/0040-4039(96)01358-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Primary, secondary and tertiary difluoroallylic alcohols underwent facile [2,3]-rearrangement upon treatment with phenylsulfenyl chloride or chlorodiphenylphosphine, to the corresponding sulfoxides and phosphine oxides. In the primary cases, the rearrangement was considerably slower, while in the tertiary cases, S(N)2' chlorination reactions competed to a significant extent. Heating the sulfoxide products with triethyl phosphite failed to induce conversion back to the allylic alcohols, consistent with the strong preference of the CF2 centre for the sp(3) hybridisation state. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码：6403 / 6406
页数：4
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