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

Yewei Yang; Xian Huang

doi:10.1021/jo800123m

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

J Org Chem. 2008 Jun 20;73(12):4702-4. doi: 10.1021/jo800123m. Epub 2008 May 24.

Authors

Yewei Yang¹, Xian Huang

Affiliation

¹ Department of Chemistry, Zhejiang University (Xixi Campus), Hangzhou, PR China.

PMID: 18500840
DOI: 10.1021/jo800123m

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.