Experiments directed towards the synthesis of anthracyclinones. V. Double Claisen rearrangement of 1, 4-Bis (allyloxy) anthraquinones

RC Cambie, H Zhen-Dong, WI Noall…

Index: Cambie; Zhen-Dong; Noall; et al. Australian Journal of Chemistry, 1981 , vol. 34, # 4 p. 819 - 828

Full Text: HTML

Citation Number: 14

Abstract

Abstract The Claisen rearrangements of 1, 4-bis (prop-2'-enyloxy) anthraquinone (4) and 1, 4-bis (2'-chloroprop-2'-enyloxy) anthraquinone (3) in o-dichlorobenzene have been examined. The former gives a low yield of 1, 4-dihydroxy-2, 3-bis (prop-2'-enyl) anthraquinone (22), and 1, 4-dihydroxy-2-(prop-2'-eny1)-anthraquinone (5) as the major product. Also formed is 1-hydroxy-4-propanoyl-2-(prop-2'-enyl)-anthraquinone (6) which ...