Bulletin of the Chemical Society of Japan p. 205 - 209 (1980)
Update date:2022-08-04
Topics:
Inagaki, Yoshio
Hosogai, Takeo
Okazaki, Renji
Inamoto, Naoki
2,4-Di-t-butyl-6-methyl-N-(thiosulfinyl)aniline (1) gave 2,4-di-t-butyl-6-methylaniline in the reactions with such reagents as alkylamines, thiourea, butyllithium, alkylmagnesium halides, 1-(1-pyrrolidinyl)cyclopentene, and hydrogen sulfide.Triphenylphosphine reacted with 1 to give (2,4-di-t-butyl-6-methylphenylimino)triphenylphosphorane and bis(2,4-di-t-butyl-6-methylphenyl)sulfur diimide.Reaction of triphenylphosphine with 2,4,6-tri-t-butyl-7,8-dithia-9-azabicyclo<4.3.0>nona-2,4,9-triene afforded 2,4,6-tri-t-butylaniline, bis(2,4,6-tri-t-butylphenyl)sulfur diimide, and 2,4,6-tri-t-butyl-N-sulfinylaniline (7).The sulfur diimide was considered to be formed via intermediary 2,4,6-tri-t-butylthionitrosobenzene, which was trapped by oxygen to give the N-sulfinyl derivative 7.
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(1980)