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

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

Source and publish data:

Tetrahedron Letters p. 5293 - 5296 (1994)

Update date:2022-07-31

Topics: Thiazole Diels-Alder Reactions Generation o-Quinodimethanes

Authors:

Potter, Andrew J.

Storr, Richard C.

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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.

Full text of DOI:10.1016/S0040-4039(00)77088-2

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