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DOI: 10.1055/s-2005-869993
Diversion from Bicyclo[4.2.0]octanol Formation Through the Use of Vinyl Electrophiles
Publikationsverlauf
Publikationsdatum:
13. Juli 2005 (online)
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Abstract
Bicyclo[4.2.0]octanols can be obtained from the reaction of phenyl vinyl sulfoxide and the lithium enolate of cyclohexanone under controlled conditions. Diversion to alkylation or Michael-Michael-ring closure was observed when alternative vinyl electrophiles were used. Novel bicyclic disulfones and hydroxyhexahydronaphthalenes were isolated. The use of a vinyl sulfoxide electrophile is crucial to the formation of bicyclo[4.2.0]octanols from simple ketones.
Key words
alkylations - bicyclic compounds - ketones - Michael additions - ring closure
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References
Atom coordinates, bond lengths, angles and thermal parameters have been deposited at the Cambridge Crystallographic Data Centre for structures 9-12 (CCDC reference numbers 265361-265364, respectively). 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).