Synthesis 2012; 44(18): 2843-2850
DOI: 10.1055/s-0031-1290822
special topic
© Georg Thieme Verlag Stuttgart · New York

Functionalized Cyclopropenes and Methylenecyclopropenes from Dianions of 3-Hydroxymethylcyclopropenes

Matthew D. Hassink
Brown Laboratories, Department of Chemistry and Biochemistry, University of Delaware, Newark, DE 19716, USA, Email: jmfox@udel.edu
,
Joseph M. Fox*
Brown Laboratories, Department of Chemistry and Biochemistry, University of Delaware, Newark, DE 19716, USA, Email: jmfox@udel.edu
› Author Affiliations
Further Information

Publication History

Received: 29 February 2012

Accepted: 09 March 2012

Publication Date:
08 May 2012 (eFirst)

Abstract

1,2-Disubstituted 3-hydroxymethylcyclopropene derivatives have been synthesized by reacting the dianions of 1-alkyl-3-hydroxymethylcyclopropenes with a range of electrophiles. Additionally, a complementary procedure is described for one-pot sequential alkylation/rearrangement to provide a convenient synthesis of a chiral methylenecyclopropane directly from a 1-alkyl-3-hydroxymethylcyclopropene.

Supporting Information

 
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