Journal of the American Chemical Society

The stereochemistry of addition of trialkylammonium and pyridinium tetrafluoroborate salts to activated acetylenes. Preparation of novel dienophiles for Diels-Alder …

ME Jung, KR Buszek

Index: Jung,M-E.; Buszek,K.R. Journal of the American Chemical Society, 1988 , vol. 110, p. 3965

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Citation Number: 51

Abstract

Abstract The preparation of a new class of dienophiles, alkenylammonium and-i" onium tetrafluoroborate salts, for Diels-Alder cycloadditions is described. The reactions between trialkylammonium and pyridinium tetrafluoroborate salts with activated acetylenes show an unusual stereochemical dependence upon steric factors, solvent, and the nature of the activating group. A reasonable mechanism for the reaction which accounts for the ...