trans -2-(dimethylaminomethyl)cyclohexylamine, 53369-74-7; 2-methyl-3-dimethylaminopropylamine, 6105-72-2; 4-methyl-3,4-diazatricyclo[5.2.1.02'6]-2-decene, 53369-75-8; 3-methyIene-2-norbornanone, 5597-27-3; methylhydrazine, 60-34-4; o-(dimethylammo'methyl)benzonitrile, 53369-76-9; o-cyanobenzyl bromide, 22115-41-9; dimethylamine, 124-40-3; o-(dimethylaminomethyl)benzylamine, 53369-77-0; o -(dimethylaminomethyl)benzylamine hydrochloride, 53369-78-1; , , ', ',2,2-hexameth-yI-l,3-propanediamine, 53369-79-2; o-bis(dimethylaminomethyl)benzene, 53369-80-5; o-bis(dimethylaminomethyl)benzene monoperchlorate, 53369-81-6.Miniprint Material Available. Full-sized photocopies of the miniprinted material from this paper only or microfiche (105 X 148 mm, 24X reduction, negatives) containing all the miniprinted and supplementary material for the papers in this issue may be obtained from the

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To seek a unique combination of anchimeric participation and electrocyclic ring opening in solvolysis reactions, a number of tosylates of the title were prepared and characterized. The anti-8 tosylates indeed do undergo hydrolysis and acetolysis with concomitant 1,4-aryl migration by the Ari-5 route and cyclopropyl ring opening to afford novel 3,syn-8-diarylbicyclo[3.2.1]oct-3-en-2-ols. The structures of these products were established by various means, among them ozonation to ci's-2-arylcyclopentane-cis-l,3-dicarboxylic acids (cí's-2-arylnorcamphoric acids). Although ~7000-fold as fast in solvolysis as their nonphenyl analogs (evidence for anchimeric participation), the anti-8 tosylates exhibit a low p value (-1.68 for hydrolysis and -1.3 for acetolysis) among themselves. This fact, together with the slight rate retardation caused by the introduction of a C-6,7 double bond, indicates considerable concertedness in the aryl migration and cyclopropyl ring opening processes. An example of a syn-8 tosylate of the title was found to rearrange differently, following a combination of paths most closely related to that reported for syn-7-norbornenyl tosylate. Because this path does not involve aryl participation in the slow step, this syn-8 tosylate was essentially equal in rate to its nonphenyl analog.

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