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Iodohydroxylation of alkylidenecyclopropanes. An efficient synthesis of iodocyclopropylmethanol and 3-iodobut-3-en-1-ol derivatives.

Authors
Type
Published Article
Journal
The Journal of organic chemistry
Publication Date
Volume
73
Issue
12
Pages
4702–4704
Identifiers
DOI: 10.1021/jo800123m
PMID: 18500840
Source
Medline

Abstract

A variety of iodocyclopropylmethanol and 3-iodobut-3-en-1-ol derivatives were readily prepared in good to excellent yields via the simple iodohydroxylation reaction of alkylidenecyclopropanes with I(2) and H(2)O. An unexpected rearrangement to give 4-hydroxy-1,2-diphenyl-butan-1-one derivatives was observed compared to the halohydroxylation products.

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