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://www.sciencedirect.com/science/article/pii/S...
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 |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 101162 |
| Deposited On: | 19 Jan 2017 06:16 |
| Last Modified: | 19 Jan 2017 06:16 |
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