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Highly selective hydrohalogenation reaction of substituted 23‐allenoates
Author(s) -
Ma ShengMing,
Wang GuangWei
Publication year - 1999
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.19990170517
Subject(s) - chemistry , combinatorial chemistry , nanotechnology , computational chemistry , materials science
The hydrohalogenation reaction of 1‐alkyl substituted 1,2‐allenyl carboxylic acid esters (1) with MX (M= Na, or Li, X= Cl, Br, I) afforded a mixture of β,γ‐unsaturated 3‐halo–3‐alkenoates (2) and Q,P unsaturated 3‐halo‐2‐alkenoates (3) in HOAc, while using a mixture of HOAC‐CF 3 CO 2 H (1:1) or CF 3 C 2 H as the reaction medium the corresponding reaction cleanly produced β,γ ‐unsaturated 3‐hale3‐alkenoates (2) as the sole products in high yields. The subsequent coupling reactions were studied.