Dasgupta, Ratna ; Kanjilal, Pranab R. ; Patra, Swapan K. ; Sarkar, Manish ; Ghatak, Usha Ranjan (1985) Condensed cyclic and bridged-ring systems : part 12: a novel synthetic route to 4-p-methoxyphenyl-bicyclo[ 2.2.2 ]octan-2-ones and some bicyclo [ 3.2.1 ] octane derivatives by acid-catalyzed intramolecula Tetrahedron, 41 (23). pp. 5619-5625. 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)91364-X
Abstract
The efficacy of a new acid-catalyzed intramolecular C-alkylation has been demonstrated by the synthesis of 1-methyl-4-P -methoxyphenylbicyclo [2.2.2] octan-2-one (5) and 4-P-methoxyphenylbicyclo [2.2.2] octan-2-one (6) from easily accessible starting materials. The carbinol 30 , derived from 5, undergoes facile rearrangement leading to 1-P-methoxyphenyl-4-methyl bicyclo [3.2.1] oct-3-ene (22), which has been transformed to endo-1-P-methoxyphenyl-4-methylbicyclo [3.2.1] octan-3-one (25).
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 28056 |
| Deposited On: | 15 Dec 2010 12:33 |
| Last Modified: | 11 Feb 2011 05:55 |
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