THIAZOLE O-QUINODIMETHANES - THE GENERATION, ELECTROCYCLIZATION AND DIELS-ALDER REACTIONS OF PHENYL-SUBSTITUTED DERIVATIVES

alpha-(2-Phenyl-4-methylthiazol-5-yl)-alpha-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 fr...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron letters Vol. 35; no. 29; pp. 5293 - 5296
Main Authors POTTER, AJ, STORR, RC
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 18.07.1994
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Online AccessGet full text

Cover

More Information
Summary:alpha-(2-Phenyl-4-methylthiazol-5-yl)-alpha-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.
ISSN:0040-4039
DOI:10.1016/S0040-4039(00)77088-2