THE CHEMISTRY OF DIPHENYLCARBENE IN POLYCRYSTALLINE (S)-2-BUTANOL. THE FORMATION OF AN ENANTIOMERICALLY PURE PRODUCT OF RADICAL-RADICAL COUPLING

Article abstract of DOI:10.1016/S0040-4039(00)94510-6

Photolysis of diphenyldiazomethane 1 in RS-2-butanol in solution between room temperature and -115 deg C gives ether 5 as only volatile product.Photolysis of 1 in polycrystalline (S)-2-butanol at -196 deg C gives 5 as well as the 5 products derived from formal CH insertion of the carbene into the matrix.Tertiary alcohol 6 was formed in 15percent yield and was shown to be enantiomerically pure.