ELECTROPHILIC SUBSTITUTION OF CYMANTRENES .3. METHOXY-, MERCAPTO-, AND THIENO-CYMANTRENES (CYMANTRENE DERIVATIVES, X)

Methoxycymantrene (3) was prepared from cymantrene diazonium sulfate via (the very oxygen sensitive) hydroxycymantrene. Mercaptocymantrene (7), which is also prone to autoxidation, can be isolated, if O2 is excluded, after reduction of the sulfonyl chloride 5. 7 yields with dimethyl sulfate methylthiocymantrene (9). The reaction with chloroacetic acid produces S-cymantrenyl thioglycolic acid (12). From 12 the ketone 14 and thence thienocymantrene (16) is accessible by cyclisation. © 1969 Springer-Verlag.