ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Thermal Rearrangement of 2-Oxa-bicyclo [3.3.1]-non-7-en-3-ones; a Novel Lactone RearrangementLactone (+)-2 was prepared by iodolactonisation and subsequent elimination in 51% yield from the known acid (+)-1 (Scheme 1). Alkylation of (+)-2 furnished (+)-3a, (+)-3b and (+)-3c, respectively (Scheme 2). Heating of (+)-3a in boiling DMF racemized the compound ((+)-3a ⇆ (-)-4a). Heating of (+)-3b and (+)-3c, respectively, equilibrated them with (-)-4b and (-)-4c, respectively. This results are interpreted as a [3.3]-sigmatropic rearrangement with a transition state as depicted in a.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19790620231