Chkraborty, Asit K. ; Saha, Bijali ; Ray, Chhanda ; Ghatak, Usha Ranjan (1987) Alkali metal-liquid ammonia reduction of γ-lactones to diols and cyclic hemiacetals: stereochemical influence by the neighbouring group on the nature Tetrahedron, 43 (19). pp. 4433-4437. 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)90319-9
Abstract
Lithium or sodium-liquid aimmonia reduction of 3-hydroxy-1,3-dimethylcyclohexane-1,3-carbolactones (5), (6) and (7 ) with or without a C-2 equatorial substituent gives the respective diols (8), (9) and (10), whereas the lactones ( 11) and (bar12 ), having a C-2 axial substituent produce the respective cyclic hemiacetals (13) and (14 ) as the sole products. A possible mechanism has been suggested for rationalisation of these results.
| Item Type: | Article |
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| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 28062 |
| Deposited On: | 15 Dec 2010 12:27 |
| Last Modified: | 11 Feb 2011 05:46 |
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