Claisen rearrangement of allyloxyanthraquinones
Keyword(s):
Allyloxyanthraquinones showed unusual behaviour during the Claisen rearrangement. Thus, 1-allyloxyanthraquinone 9 rearranged very readily in the presence of benzylamine while 2-allyloxyanthraquinone 13 refused to do rearrangement even under very drastic conditions. On the other hand, 1,2-diallyloxyanthraquinone rearranged with the loss of the 2-allyloxy group as the result of a retro-ene reaction which has not been previously observed while 1,4-di(2′-chloro-2′-propenyloxy)anthraquinone 18 rearranged to give, as a major product, the unsymmetrically substituted anthraquinone 19 which is useful in the synthesis of anthracycline aglycones.