cc=c

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[CONTRIBUTION PROM

THE

DEPARTMENT OF CHEMISTRY, COLUMBIA

UNIVERSITY

The Rearrangement of Allyl Groups in Three-carbon Systems. IV.

]

Hydrocarbons

BY HAROLD LEVYAND ARTHURC. COPE The following thermal rearrangement has been Evidently, a single phenyl group provides suffiobserved to occur in enough instances to estab- cient activation for the rearrangements. Proof lish the reaction as fairly general when X and JT of the structuies of the pairs, V ---f VI and VI1 VIII, shows that in these rearrangements the allyl are CN or COOC2H6' group undergoes inversion. - f P a Y P " The aliphatic diolefin, IX, also rearranged, alI I /X 135-200O i I X -c=c-c, ___ic -c-c=c