Studies in bicyclo[3.1.0]hexane methanolysis. Ring opening of activated cyclopropanes under acidic and basic conditions.
A bicyclo[3.1.0]hexane, with one cyclopropane carbon flanked by a ketone and an ester or an aldehyde, undergoes methanolysis with cleavage of one of the two activated cyclopropane bonds, depending on the reaction conditions. Acidic conditions yield primarily or exclusively a 4-methoxycyclohexane, while basic conditions yield a 3-methoxymethylcyclopentanone.
Department of Chemistry, 1901 N. 13th Street, Temple University, Philadelphia, Pennsylvania 19122, USA.
Yeon-Hee
YH
Lim
Kevin F
KF
McGee
Scott McN
SM
Sieburth
D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D003500:Cyclization; D003521:Cyclopropanes / Q000737:chemistry*; D006586:Hexanes / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D000432:Methanol / Q000737:chemistry*; D015394:Molecular Structure
D001643:Bridged Bicyclo Compounds; D003521:Cyclopropanes; D006586:Hexanes; D000432:Methanol