Bleach/acetic acid-promoted chlorinative ring expansion of [2.2.1]- and [2.2.2]-bicycles.
[formula: see text] Treatment of vinyl-substituted [2.2.1]- and [2.2.2]-bicyclocarbinols with NaOCl and AcOH provides [3.2.1]- and [3.2.2]-beta-chloro-bicycloketones, respectively. For [2.2.2]-bicycles, these chlorinative ring expansions are particularly efficient and selective.
Ruggles
Erik L
EL
Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA.
Maleczka
Robert E
RE
D019342:Acetic Acid / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D002713:Chlorine / Q000737:chemistry; D015394:Molecular Structure; D012973:Sodium Hypochlorite / Q000737:chemistry
D019086:Bridged Bicyclo Compounds, Heterocyclic; D002713:Chlorine; D012973:Sodium Hypochlorite; D019342:Acetic Acid