Bimolecular Intermolecular-Michael/Intramolecular-Michael/Aromatization Reaction of 1-Cyanocyclopropane 1-Esters or 1,1-Dicyanocyclopropanes: A Straightforward Approach to Fully Substituted Benzenes

Weijian Ye; Lanxiang Zhou; Shuwen Xue; Yang Li; Cunde Wang

doi:10.1055/s-0034-1379909

Synlett, Table of Contents

Synlett 2015; 26(12): 1769-1773
DOI: 10.1055/s-0034-1379909

letter

Bimolecular Intermolecular-Michael/Intramolecular-Michael/Aromatization Reaction of 1-Cyanocyclopropane 1-Esters or 1,1-Dicyanocyclopropanes: A Straightforward Approach to Fully Substituted Benzenes

Weijian Ye

School of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Street, Yangzhou 225002, P. R. of China Email: wangcd@yzu.edu.cn

,

Lanxiang Zhou

School of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Street, Yangzhou 225002, P. R. of China Email: wangcd@yzu.edu.cn

,

Shuwen Xue

School of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Street, Yangzhou 225002, P. R. of China Email: wangcd@yzu.edu.cn

,

Yang Li

School of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Street, Yangzhou 225002, P. R. of China Email: wangcd@yzu.edu.cn

,

Cunde Wang*

School of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Street, Yangzhou 225002, P. R. of China Email: wangcd@yzu.edu.cn

› Author Affiliations

Abstract

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Abstract

An efficient and straightforward synthetic protocol has been developed for the preparation of fully substituted benzenes via a [3+3]-cyclodimerization reaction of 1-cyanocyclopropane 1-esters or 1,1-dicyanocyclopropanes for the generation of a wide range of structurally interesting significant compounds. The reaction utilizes Et₃N-promoted C–C bond cleavage, two new C–C bond formations of 1-cyanocyclopropane 1-ester and simultaneous aromatization by removal of cyano and ester groups in a domino fashion.

Key words

[3+3]-cyclodimerization - donor–acceptor cyclopropane - 1-cyanocyclopropane 1-ester - fully substituted benzene - aromatization

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References

References and Notes
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