Synthesis 2006(21): 3605-3610  
DOI: 10.1055/s-2006-950215
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Multifunctionalized Furans from Diazoallenes: Rearrangement of 6-Methylenebicyclo[3.1.0]hexanes

Tuanli Yao, Allen Hong, Richmond Sarpong*
Department of Chemistry, University of California, Berkeley, CA 94720, USA
Fax: +1(510)6429675; e-Mail: rsarpong@berkeley.edu;
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Publication History

Received 30 May 2006
Publication Date:
21 August 2006 (online)

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Abstract

The synthesis of annulated tetrasubstituted furans using diazoallene precursors is described. This reaction provides efficient access to synthetically useful furan intermediates, which are otherwise difficult to obtain.

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The diazoallene compounds were found to be unstable using EI techniques for mass spectrometry measurements.