Synthesis of Some Conjugated Caradienes from 3-Carene by the Wittig Reaction and Their Reactivity in the Diels-Alder Reaction

Article abstract of DOI:10.1016/S0040-4020(01)89328-5

The applicability of the Wittig reaction for the preparation of conjugated cis-caradienes was studied by the preparation of 4-methyl-3(10)-carene (27).The method was applied for the study of the synthesis of 3-vinyl-3-apocarene (6), 4-methylene-3(10)-carene (7), 4-methyl-2-methylene-3(10)-carene (8), 4-isopropenyl-3-carene (9) and 4-isopropenyl-3-caren-2a-ol (11) starting from 3-carene (20).The reactivity of conjugated cis-caradienes 6,7 and 9 in the Diels-Alder reaction has also been studied.