The Journal of Organic Chemistry

Mechanistic impact of oxime formation accompanying 1, 3-dipolar cycloadditions of nitrile oxides

J Baran, H Mayr

文献索引：Baran, Janusz; Mayr, Herbert Journal of Organic Chemistry, 1989 , vol. 54, # 21 p. 5012 - 5016

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被引用次数: 17

摘要

Benzonitrile oxide (la) reach with 1, 1, 2, 2, 3, 3-hexamethyl-4, 5-bis (methylene) cyclopen~ e (5) to give a mixture of the 1, 3-dipolar cycloaddition product 8 and the oxime 9. This reaction is 26 times slower than the corresponding reaction of la with 1, 2-bis (methylene) cyclopentane (15), which exclusively yields the 2-isoxazoline 19. With the assumption that the oxime 9 is generated by a stepwise process, one can estimate that the barrier for the ...