Peruncheralathan, S. ; Sriram, V. ; Ila, H. ; Junjappa, H. (2004) Domino carbocationic rearrangements of α-[bis(methylthio)methylene]alkyl-2-(heteroaryl)cyclopropyl ketones Tetrahedron, 60 (26). pp. 5603-5612. ISSN 0040-4020
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...
Related URL: http://dx.doi.org/10.1016/j.tet.2004.04.048
Abstract
Domino carbocationic rearrangements of α-[bis(methylthio)methylene]alkyl-2-(heteroaryl)cyclopropyl ketones (X=O, S, NMe) bearing five-membered heteroaryl group have been investigated. Although the cyclopropyl ketones (R1=H) gave similar products like their aryl counterparts under these conditions, the corresponding α-methylcyclopropyl ketones (R1=Me) yielded a variety of unexpected products depending on the nature of heteroaryl group in the substrate cyclopropyl ketones and the type of acid catalyst used. A probable mechanism for the formation of various products in these transformations has been proposed.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Heteroarylcyclopropyl Ketones; Domino Carbocationic Rearrangement; α-Oxoketene Dithioacetals; Cyclopentano[b]fused Heterocycles |
| ID Code: | 15323 |
| Deposited On: | 13 Nov 2010 12:56 |
| Last Modified: | 03 Jun 2011 04:44 |
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