Camphenilyl derivatives

The corresponding camphenilyl derivatives (28, 29) reveal an even higher exo endo rate ratio31. ... 

The formation of a-terpineol as the major product from deamination of fenchyl amine (43-NH2) (98) is remarkable in that it requires first rearrangement to the more strained pinane skeleton. Small amounts (3—11%) of pinane-type products have been isolated from the bornyl and fenchyl diazonium ions under alkaline conditions (98 a). The contra-thermodynamic rearrangement of apobornyl and camphenilyl derivatives to nopinone may be effected in good yield with the driving force of the pinacol-type rearrangement (98 b, 99). 

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