ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Structure Elucidation of a Product of Intramolecular Diels-Alder-Reaction: Configurational and Conformational Analysis of 5-Methyl-2-phenyl-1H,2,3,3a,4,5,7a-hexahydroisoindol-1-oneN-Allyl-N-phenylsorbamide 1 cyclizes at 160°C to give 5-methyl-2-phenyl-1H,2,3,3a,4,5,7a-hexahydroisoindol-1-one 2. As a result of this intramolecular [4 + 2] cycloaddition four stereoisomeres 2a-2d can exist. The 1H and 13C n.m.r. data are given. The 1H n.m.r. studies demonstrate that the product of Diels-Alder cyclisation is the result of cis-fusion of the two rings. The nuclear Overhauser effect data provide further evidence for 2a in which the carbonyl group and methyl one are trans-arranged. The n.m.r. results are confirmed by X-ray studies.
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19863280405