Design and synthesis of N-vinylacetamide derivative with bulky group by nucleophilic substitution reaction

Cyclohexyl, adamantyl, and triphenylmethyl groups were employed for the nucleophilic substitution reaction with N-vinylacetamide (NVA), in order to investigate the bulky substituents effects on molecular structures in N-vinyl monomers. Although normal alkyl halides were known to produce N-substituted NVA, alkyl halides with secondary and tertiary carbons did not occur nucleophilic substitution reaction. On the contrary, triphenylmethyl group was introduced into β-position on NVA, accompanied with hydrogen transfer. The refined crystal structure of β-triphenylmethyl-N-vinylacetamide revealed intermolecular linear hydrogen bonds and aromatic bulky triphenylmethyl group supported the structure.