Abstract
The 2-alkylimino-1,3-oxathiolanes are known to readily undergo methylation at imine nitrogen [1]; however they are not regarded as alkylating agents. We found that 2-(1-adamantylimino)-5-methyl-1,3oxathiolane (I) could be applied to alkylation of aromatic compounds. The reaction of oxathiolane I with pand m-xylene (IIa, b) in the presence of aluminum chloride gave rise to 2-arylpropyl thiocarbamates IIIa, b. The splitting of the adamantyl moiety may be ascribed to the high stability of the corresponding carbocation that alkylates the xylene present in excess. The formation of a mixture of isomeric hydrocarbons is due to probable isomerization on the aluminum chloride both of the original xylenes [2] and the adamantylxylenes. Reaction products IIIa, b do not suffer isomerization presumably because of complex formation at the functional group with aluminum chloride. Unlike pand m-xylene
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