Balu, Maliakel P. ; Ila, Hiriyakkanavar ; Junjappa, Hiriyakkanavar (1990) Studies on cycloaddition reactions of 1,3-diphenyl-2-azaallyl lithium and ethyl (benzylideneamino) acetate anion with α-oxoketene dithioacetals Tetrahedron, 46 (19). pp. 6771-6782. ISSN 0040-4020
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...
Related URL: http://dx.doi.org/10.1016/S0040-4020(01)87865-0
Abstract
The α-oxoketene dithioacetals undergo anionic [1,3] cycloaddition with l,3-diphenyl-2-azaallyllithium to give either pyrroles or spiropyrrolines with two exceptions. Lithium bromide/triethylamine induced cycloaddition of ethyl (benzylideneamino)acetate (7̲) with acyclic ct-oxoketene dithioacetals afforded either pyrrolidine, pyrrole or the corresponding 3-benzylideneamino-pyran-2-one derivatives depending on the reaction conditions and the structural variations in the a- oxoketene dithioacetals. Nitroketene dithioacetal also underwent anionic [1,3]cycloaddition with either 1̲ or 7̲ under described conditions to afford pyrrolidine or pyrrole derivatives. Probable mechanisms for the formation of various products are suggested.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 15333 |
| Deposited On: | 13 Nov 2010 12:55 |
| Last Modified: | 22 Feb 2011 08:51 |
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