Bis(carbomethoxy)maleic Anhydride

Article abstract of DOI:10.1021/jo00140a010

Bis(carbomethoxy)maleic anhydride (1) was synthesized by phosphoric anhydride induced demethoxylation of tetramethyl ethylenetetracarboxylate.With p-methoxystyrene, anethole, divinylbenzene, and diphenylethylene, 1 formed 2:1 Diels-Alder adducts.With styrene and isobutyl vinyl ether, 1 underwent an inverse electron-demand Diels-Alder reaction leading to 3,4-dihydro-2H-pyran derivatives.In the Diels-Alder reaction with butadiene, 1 was 100 times less reactive than (carbomethoxy)maleic anhydride.A radical-initiated alternating copolymer was obtained at 80 deg C with styrene.