Journal of Organic Chemistry p. 5239 - 5243 (1980)
Update date:2022-09-26
Topics:
Roberts, John T.
Rittberg, Barry R.
Kovacic, Peter
Scalzi, Francis V.
Seely, Michael J.
N,N-Dihalo derivatives of (1-adamantyl)- and neopentylamine are converted to the corresponding alkyl halides in excellent yields (88-94percent) during GLC at 155-330 deg C.Decomposition apparently occurs by an SNi mechanism or by intramolecular homolytic cleavage.Intermolecular radical and free-ion reactions are eliminated from consideration because of the absence of radical-derived or rearranged products.Steric factors are deemed important in the neopentyl case since pyrolysis of N,N-dihalo<(1-adamantyl)methyl>amine gave the corresponding carbonitrile in excellent yield(90-97percent). 1-(Haloamino)adamantanes gave fair amounts of 1-haloadamantanes (30-38percent). 1-(Acetylamino)- and 1-(ethylchloroamino)adamantane yielded 1-chloroadamantane (10-17percent), the major products being the acetamide (60percent) and the ethylamine (56percent), respectively. 1-(Dihaloamino)adamantanes were converted to 1-haloadamantanes by neat (64-70percent) or solution (30-41percent) pyrolysis.
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