Direct synthesis of substituted naphthalenes from 1,3-dicarbonyl compounds and 1,2-bis(halomethyl)benzenes including a novel rearrangement aromatization of benzo[c]oxepine

Jun-gang Wang; Meng Wang; Jia-chen Xiang; Yan-ping Zhu; Wei-jian Xue; An-xin Wu

doi:10.1021/ol302950w

Direct synthesis of substituted naphthalenes from 1,3-dicarbonyl compounds and 1,2-bis(halomethyl)benzenes including a novel rearrangement aromatization of benzo[c]oxepine

Org Lett. 2012 Dec 7;14(23):6060-3. doi: 10.1021/ol302950w. Epub 2012 Nov 27.

Authors

Jun-gang Wang¹, Meng Wang, Jia-chen Xiang, Yan-ping Zhu, Wei-jian Xue, An-xin Wu

Affiliation

¹ Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Hubei, Wuhan 430079, P. R. China.

PMID: 23186000
DOI: 10.1021/ol302950w

Abstract

An unexpected rearrangement aromatization of benzo[c]oxepine has been revealed to synthesize substituted naphthalenes. This observation was further exploited to develop an efficient approach for the construction of naphthalenes from simple and commercially available 1,3-dicarbonyl compounds and 1,2-bis(halomethyl)benzene compounds via a new domino reaction sequence.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzene Derivatives / chemistry*
Benzoxepins / chemistry*
Catalysis
Hydrocarbons, Halogenated / chemical synthesis
Hydrocarbons, Halogenated / chemistry*
Ketones / chemical synthesis*
Ketones / chemistry*
Molecular Structure
Naphthalenes / chemical synthesis*
Naphthalenes / chemistry

Substances

Benzene Derivatives
Benzoxepins
Hydrocarbons, Halogenated
Ketones
Naphthalenes