Khan, Faiz Ahmed ; Hari Mangeswara Rao, G. ; Satapathy, Rashmirekha ; Parasuraman, Karuppasamy (2007) Serendipitously discovered diazomethane-mediated novel molecular rearrangements of norbornyl α-ketohemiketals Organic Letters, 9 (8). pp. 1581-1584. ISSN 1523-7060
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Official URL: http://pubs.acs.org/doi/abs/10.1021/ol070442g
Related URL: http://dx.doi.org/10.1021/ol070442g
Abstract
Unprecedented molecular rearrangements during diazomethane-mediated reaction of norbornyl α-ketohemiketals leading to novel molecular entities are presented. A dramatic change in the reaction outcome was noted for five- and six-membered α-ketohemiketals: the former predominantly furnished rearranged bicyclic products involving migration of the γ-alkoxy group, and the latter furnished the oxetane derivative as the major product. Interestingly, six-membered O-methyl-ketal yielded a product arising from the migration of the vicinal alkoxy group.
Item Type: | Article |
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Source: | Copyright of this article belongs to American Chemical Society. |
ID Code: | 80341 |
Deposited On: | 31 Jan 2012 14:28 |
Last Modified: | 31 Jan 2012 14:28 |
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