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The stereochemistry of the diels-alder reaction of heterodienophiles. The conformation of six-membered rings: (1,2)

✍ Scribed by Ralph Daniels; Karl A. Roseman


Publisher
Elsevier Science
Year
1966
Tongue
French
Weight
285 KB
Volume
7
Category
Article
ISSN
0040-4039

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✦ Synopsis


The recent appearance of a communication (3) dealing with results we reported at a meeting early this year (2) prompts us to present additional data we have obtained.


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The stereochemistry of the Diels-Alder reactions of 3 cyclopropenes was determined unequivocally by X-ray and NOE studies. Tetrachlorocyclopropene yields exo-adducts with (r)-l-R-1,3-butadiene (R=OCH3, OCOCH3, OSiMe ), with 1,4\_diphenylbutadieKand with furan. 1,2-bromochlorocyclopropene yields with

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It is of interest to consider the restraints imposed on the stable conformation of a six-membered ring by the presence of a planar group forming part of the ring and how the specific dimensions of the planar group may determine the conformational selection. The principal groups for which evidence i