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Synthesis 1989; 1989(6): 428-434
DOI: 10.1055/s-1989-27274
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Preparation of 3-Cycloheptenyl and 3-Cyclooctenyl Derivatives by Solvolysis of Bicyclo[n.2.0]alkyl Esters

Chrong-Shiong Hwang* , William Reusch
  • *Department of Chemistry, Michigan State University, East Lansing, MI 48824, USA
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Publication Date:
17 September 2002 (online)

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Ester derivatives of 6-substituted cis-bicyclo[3.2.0]heptan-6-ol, and of 7-substituted cis-bicyclo[4.2.0]octan-7-ol were solvolyzed to the corresponding cycloheptene and cyclooctene products. In general, acetolysis of the 3,5-dinitrobenzoates in glacial or aqueous acetic acid proved most effective for this transformation. The conjugated dienes obtained from geminal alkenylhydroxy starting materials were sensitive to polymerization and/or olefin isomerization, but were sufficiently stable to permit spectroscopic characterization and subsequent reaction with dienophiles.

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