Intramolecular trapping of an oxacarbene intermediate in the photochemical ring expansion of a cyclopentanone
Abstract
Ultraviolet irradiation of syn-5-hydroxymethyl-4, anti-5-dimethyltricyclo[2.2.1.02,6]heptan-3-one 4 in benzene or methanol gives the ring-expanded cyclic acetal 5 in high yield, establishing that the reaction proceeds via an oxacarbene intermediate.