Reaction of N-(p-Tolylsulfonyl)diphenylcyclopropenimine with Pyridinium and Isoquinolinium Ylides

Article abstract of DOI:10.1021/jo00155a031

N-(p-Tolylsulfonyl)diphenylcyclopropenimine (2) reacted smoothly with pyridinium N-carbethoxyamide (3) to afford a new ylide (5), in addition to stilbene 4, uracil 6, and pyrimidone 7.An observed thermal transformation of 5 to 6 and 7 is discussed.Reaction of the cyanocarboethoxy methylides 15a-c with 2 produced the internal salts 16a-c, while the dicarbethoxy, monocarbethoxy, and benzoyl methylides 15d-f gave the pyridine-free cyclics 26, 28, and 29, respectively.The isoquinolinium methylides 31a-c reacted in an analogous fashion, while the N-amides 33a,b afforded cycloadducts 34a,b.A series of reactions used to correlate the structures of the latter is described, including an observed cycloaddition mode for diphenylcyclopropenone (1) with 33a-c which yielded 39, 37, and 42, respectively.