Memoirs of the Faculty of Engineering, Yamaguchi University

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Memoirs of the Faculty of Engineering, Yamaguchi University Volume 40 Issue 2
published_at 1990-03

Reaction of 2-Dialkylamino-1,3-oxathioran-2-ylium Salts with Nucleophilic Reagents

2-ジアルキルアミノ-1, 3-オキサチオラン-2-イリウム塩の反応
Fujisaki Shizuo
Hanada Kazuyuki
Nishida Akiko
Kajigaeshi Shoji
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KJ00000156802.pdf
Descriptions
Reactions of 2-dialkylamino-1,3-oxathioran-2-ylium prechlorates [3], five-membered ring's trihetero-substituted carbonium salts, with several nucleophiles were carried out. As the results of these treatments, it turned out that [3] had ambident properties, and 2-position of [3] became hard electrophilic center and 5-position of [3] became soft electrophilic center. That is, hard bases such as hydroxide ion, alkoxide ion, and acetoxide ion attacked upon the 2-position, and soft bases such as p-tolylmercaptide ion, N, N-dimethyldithiocarbamate ion, isocyanate ion, and cyanide ion acttacked upon the 5-position according to the HASB-Rule. Furthermore, aniline, moderate base, attacked upon the 2-position.