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Scientific article
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The Homoallyl-Cyclopropylcarbinyl Cation Rearrangement in the Solvolyses of exo- and endo-5-Norbornen-2-yl p-Bromobenzenesulfonates. Application of ²H-NMR. Spectroscopy

Published inHelvetica chimica acta, vol. 63, no. 4, p. 1006-1015
Publication date1980-06-06
Abstract

The buffered trifluoroethanolyses and acetolyses of exo-(2-D)- (6) and endo-(2-D)-5-norbornen-2-yl brosylates (7) yielded exo-5-norbornen-2-yl and 3-nortricyclyl derivatives. The deuterium distribution in these products was determined unambiguously by ²H-NMR. and MS. In contrast to previous reports, each hydrogen and, consequently, each deuterium atom could be identified. Product ratio and label distribution in the solvolysis of 6 make unnecessary the intervention of asymmetrical homoallylic cation intermediates. The results are most economically rationalized by invoking symmetrical 3-nortricyclyl ion-pair intermediates.

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Citation (ISO format)
BURGER, Ulrich, SONNEY, Jean-Marie, VOGEL, Pierre. The Homoallyl-Cyclopropylcarbinyl Cation Rearrangement in the Solvolyses of exo- and endo-5-Norbornen-2-yl p-Bromobenzenesulfonates. Application of ²H-NMR. Spectroscopy. In: Helvetica chimica acta, 1980, vol. 63, n° 4, p. 1006–1015. doi: 10.1002/hlca.19800630429
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ISSN of the journal0018-019X
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