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Studies of N-sulfinyl compounds. II. : Reaction of N-sulfinylanilines with cyclic nitrones

✍ Scribed by Otohiko Tsuge; Masashi Tashiro; Shuntarō Mataka

Book ID
104213822
Publisher
Elsevier Science
Year
1968
Tongue
French
Weight
184 KB
Volume
9
Category
Article
ISSN
0040-4039

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✦ Synopsis

It is well known that. N-sulfinylaniline reacts as a 1,34ipolarophil with benzonitril oxide(') and with diphenylnitrilimine. (3) Stark and Ratcliffe(4) reported that N-sulfinylbensenesulfonamide reacted with CN-diphenylnitrone to give N-benzenesulfonyl-N,N'-diphenylformamidine under the elimination of sulfur dioxide and migration of the phenyl group from carbon to nitrogen. Recently, we found that N-sulfinylanilines (I) reacted with ethylenecarbonate under the influence of lithium bromide or tatraethylammonium bromide to afford the corresponding N,N'-diarylpiperazines. (1)

Consequently, it may be expected that I reacts with cyclic nitrones (II), which can behave as 1,3-dipolar reagents, (5) to give either bicyclic 1,2,3,5thioxadiazoline l-oxide (III),.or tricyclic tetrazine compound (IV) by the dimerization of the intermediate which is formed under the subsequent elimination of sulfur dioxide from III (Scheme 1).

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