Generation and reactions of carbene bearing unprotected hydroxy groups at α-position

Abstract

Irradiation of 1,1-dimethyl-2-diazo-2-phenylethanol (1a) either in cyclohexane or in hexene produced 1,1-dimethyl-2-oxo-2-phenylethanol (3a), 2,2-dimethyl-3-phenyloxirane (4a), and 3-phenylbutan-2-one (5a), similarly irradiation of (1a) in methanol gave 1,1-dimethyl-2-methoxy-2-phenylethanol (6a) and 1-methoxy-2-methyl-1-phenylpropene (7a) at the expense of (3a) and (5a), all of which were derived from the carbene (2a) generated by elimination of N₂ from (1a); the corresponding reaction of (1-hydroxy)cyclohexylphenylcarbene (2b) is also described.