Synthesis of 10-alkyl-9-allenylanthracenes involving [3,4]sigmatropic rearrangement
Abstract
A synthesis of 10-alkynyl-9-allenylanthracenes (and related 10-alkenyl and 10-benzyl analogues)via acid catalysed [3,4]sigmatropic rearrangement of e.g. 10,10-dialkynyl-9-anthranols is reported; the migratory aptitudes of allyl, benzyl, and prop-2-ynyl groups is discussed.