BASE-CATALYZED REARRANGEMENT OF P-MENTH-1-EN-4(8)-OXIDE

Authors
ROY A GURUDUTT KN RAO S
Citation
A. Roy et al., BASE-CATALYZED REARRANGEMENT OF P-MENTH-1-EN-4(8)-OXIDE, Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry, 34(7), 1995, pp. 636-638
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry → ACNP
ISSN journal
03764699
Volume
34
Issue
7
Year of publication
1995
Pages
636 - 638
Database
ISI
SICI code
0376-4699(1995)34:7<636:BROP>2.0.ZU;2-Q
Abstract
p-Menth-1-en-4(8)-oxide (1), a tetrasubstituted spiro epoxide is norma lly resistant towards bases but under forcing condition with AIP rearr anges to p-mentha-1,8-dien-4-ol (2). On the other hand, with t-BuOK, p -mentha-1,3-dien-8-ol (3) and p-mentha-1,4-dien-8-ol (4) are formed as the major products. These compounds readily get oxidised to p-cymen-8 -ol (5), as seen in the reaction of 1 with N-LiEDA.