32456-89-6Relevant articles and documents
Chemical syntheses of syn- and anti-1,2;3,4-diepoxides derived from 1,4-dimethyl-and 1,2,3,4-tetramethylanthracenes and naphthalenes
Rigaudy, Jean,Lachgar, Mohamed,Caspar, Alain,Chassagnard, Claude
, p. 481 - 490 (2007/10/03)
Chemical isomerization of 1,4-endoperoxides 1a,b,n derived from meso-unsubstituted 1,4-dimethyl- or 1,2,3,4-tetramethylanthracenes (and naphthalenes) to syn-1,2;3,4-diepoxides 2a,b,n has been achieved by treatment at room temperature with FeSO4 in CH3CN containing pyridine. With analogous 9,10-diphenyl derivatives 1c,d, heating appears necessary and the same isomerization is then superseded by another type of rearrangement leading to dihydronaphthoxanthenols 4c,d. An electron-exchange mechanism may explain the difference between both series. In contrast, the isomeric anti-1,2;3,4-diepoxides 19b,c,d,n have been prepared by direct epoxidation of the hydrocarbons 18a-d,n with dimethyldioxirane generated in situ. In this case, the reaction is more efficient for 9,10-diphenyl derivatives 18c,d than for meso-unsubstituted ones 18a,b as the latter can undergo competitive oxidations at meso-positions leading to 10-hydroxy-9-anthrones 22a,b at the same time as anthraquinones 23a,b. Elsevier.