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- W2034804416 abstract "L'acétolyse des brosylates de cycloheptylméthyle 1b et de cyclooctylméthyle 1c est environ 4 fois plus rapide, à 80°, que celle du brosylate d'isobutyle: il semble que ceci soit dû à une participation de l'hydrogène en β. Les brosylates de cycloheptène-4 yl méthyle 2b et de cyclooctène-4 yl méthyle 2c s'acétolysent, avec participation de la double liaison, respectivement 250 et 350 fois plus rapidement, à 80°, que le brosylate d'isobutyle et conduisent principalement aux acétates d'endo bicyclo[3.2.1]octyle-2 8a et d'endo bicyclo[3.3.1]nonyle-2 11a, respectivement. L'acétolyse du brosylate de cyclohexène-3 yl méthyle 2a se fait sans participation et conduit à l'acétate de cyclohexène-3 yl méthyle 7. Cycloheptylmethyl brosylate (1b) and cyclooctylmethyl brosylate (1c) undergo acetolysis at 80°, about four times faster than isobutyl brosylate; this acceleration appears to be due to β-hydrogen participation. 4-Cycloheptenylmethyl brosylate (2b) and 4-cyclooctenylmethyl brosylate (2c) undergo acetolysis at 80°, with double bond participation, 250 and 350 times faster than isobutyl brosylate, respectively, the major products being endo 2-bicyclo[3.2.1]octyl acetate 8a and endo 2-bicyclo[3.3.1]-nonyl acetate 11a. Acetolysis of 3-cyclohexenylmethyl brosylate (2a) leads (without participation) to 3-cyclohexenylmethyl acetate (7)." @default.
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- W2034804416 date "1972-01-01" @default.
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- W2034804416 title "Influence de la taille du cycle sur le mecanisme de l'acetolyse de p-bromobenzenesulfonates de cycloalkylmethyle et de cycloalkenylmethyle" @default.
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- W2034804416 doi "https://doi.org/10.1016/0040-4020(72)88087-6" @default.
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