Pyrolysis and UV photoelectron spectroscopy of bicyclo[3.2.0]hept-6-en-2-one; preparation and detection of cyclohepta-2(Z),4(E)-dien-1-one.

Abstract

Flash vacuum pyrolysis of bicyclo[3.2.0]hept-6-en-2-one (1) in the source chamber of a UV photoelectron (PE) spectrometer using a CW CO2 laser as a directed heat source facilitated an electrocyclic ring expansion to yield the transient species cyclohepta-2(Z),4(E)-dien-1-one (2), the PE spectrum of which was compared to that of an authentic sample of cyclohepta-2(Z),4(Z)-dien-1-one (4) and confirmed a conrotatory ring opening of 1 that obeys the Woodward-Hoffmann rules.