Mechanistic impact of oxime formation accompanying 1, 3-dipolar cycloadditions of nitrile oxides
J Baran, H Mayr
Index: Baran, Janusz; Mayr, Herbert Journal of Organic Chemistry, 1989 , vol. 54, # 21 p. 5012 - 5016
Full Text: HTML
Citation Number: 17
Abstract
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 ...
Related Articles:
Copper (II)-mediated oxidation of 1, 2-dioxime to furoxan
[Das, Oindrila; Paria, Sayantan; Paine, Tapan Kanti Tetrahedron Letters, 2008 , vol. 49, # 41 p. 5924 - 5927]
The conversion of α-keto acids and of α-keto acid oximes to nitriles in aqueous solution
[Arai, Noriyoshi; Iwakoshi, Mitsuhiko; Tanabe, Katsuhiko; Narasaka, Koichi Bulletin of the Chemical Society of Japan, 1999 , vol. 72, # 10 p. 2277 - 2285]
[Kelly, David R.; Baker, Simon C.; King, David S.; Silva, Deepa S. de; Lord, Gwyn; Taylor, Jason P. Organic and Biomolecular Chemistry, 2008 , vol. 6, # 6 p. 787 - 796]
The Reaction of Sodium Nitrite with Ethyl Bromoacetate and with Benzyl Bromide1, 2
[Kornblum; Weaver Journal of the American Chemical Society, 1958 , vol. 80, p. 4333,4337]