Regioselective Synthesis and Diels-Alder Reaction of 3, 4-Dimethylpenta-1, 3-diene. Conformational Study of Bicyclic Adducts Structures by 1H NMR (NOESY, ASIS) …

P Gosselin, C Bourdy, S Mille…

文献索引：Gosselin, Pascal; Bourdy, Christophe; Mille, Stephane; Perrotin, Angelique Journal of Organic Chemistry, 1999 , vol. 64, # 26 p. 9557 - 9565

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被引用次数: 13

摘要

A three-step, regioselective synthesis of 3, 4-dimethylpenta-1, 3-diene 1 has been developed. The condensation of acetone diethylacetal with ethyl propenyl ether yielded, after hydrolysis of the resulting triethoxy adduct 10, 2, 3-dimethyl-2-butenal 7. Wittig reaction of 7 with methylenetriphenylphosphorane afforded desired diene 1 in 31% overall yield, easily scalable to the 10 g level. Diels-Alder reaction of 1 with maleic anhydride in ...

~85%

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