Synthesis 2006(21): 3639-3646  
DOI: 10.1055/s-2006-950312
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Cyclopropanes via Organoiron Methodology: Preparation and Rearrangement of Divinylcyclopropanes - Studies Directed toward the Synthesis­ of Hydroazulenes

Nathaniel J. Wallocka, Dennis W. Bennettb, Tasneem Siddiqueeb, Daniel T. Hawortha, William A. Donaldson*a
a Department of Chemistry, Marquette University, P. O. Box 1881, Milwaukee, WI 53201-1881, USA
b Department of Chemistry and Biochemistry, University of Wisconsin-Milwaukee, Milwaukee, WI 53201-0413, USA
Fax: +1 (414)288 7066; e-Mail: william.donaldson@marquette.edu;
Further Information

Publication History

Received 25 August 2006
Publication Date:
09 October 2006 (online)

Abstract

Addition of alkenyl Grignard reagents to (1-methoxycarbonylpentadienyl)iron(1+) cation generates the corresponding (2-alkenylpent-3-en-1,5-diyl)iron complexes. Oxidatively induced reductive elimination of these complexes gives divinylcyclopropanes which can undergo subsequent Cope rearrangement to give 1,4-cycloheptadienes.

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The crystallographic data for 5a has been deposited with the Cambridge Crystallographic Data Center; CCDC No. 237614. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax (+44)1223 336033; email: deposit@ccdc.cam.ac.uk].