Thiazole o-quinodimethanes: The generation, electrocyclisation and Diels-Alder reactions of phenyl substituted derivatives

Article abstract of DOI:10.1016/S0040-4039(00)77088-2

α-(2-Phenyl-4-methylthiazol-5-yl)-α-phenylmethyl acetate 2 undergoes thermal elimination of acetic acid to give the o-quinodimethane 3. In solution this can be intercepted in Diels-Alder reactions but under flash pyrolytic conditions naphthalene-2-thiol is formed by electrocyclisation and fragmentation.