PHOTOSENSITIZED REACTIONS OF 1-CYCLOHEXENYL CARBINOLS

Dimethyl-1-cyclohexenylcarbinol (1a) affords a mixture of methylcyclohexane (8%). methylenecyclohexane (2%). 1-methylcyclohexanol (5%). isopropylidenecyclohexane oxide (10%). and 2-(1-hydroxycyclohexyl)-2-propanol (20%) upon UV irradiation in aqueous t-butyl alcohol with m-xylene as the photosensitizer. Under the same conditions 1-cyclohexenylmethanol (1b) yields methylenecyclohexane oxide (trace), cyclohexylmethanol (20%). and 1-hydroxymethyl-1-cyclohexanol (25%). Possible pathways to these various products are proposed. © 1969.