In previous investigations 'soft' nucleophiles in the form of arene oxides have been observed to attack alkynyliodinium salts in a Michael-type reaction to generate alkylidinecarbene intermediates which primarily undergo a 1,5-intramolecular C-H insertion reaction to afford benzofurans.  In our investigations we have observed that 1H-1-(1-alkynyl)-5-methyl-1,2,3-benziodoxathiole 3,3-dioxides bearing aliphatic alkynyl groups instead produce products of aliphatic 1,5-intramolecular C-H insertion or products derived from alkenyliodonium salts upon treatment with arene oxides.

Divergent reactivity towards nucleophiles in 1H-1-(1-alkynyl)-5-methyl-1,2,3-benziodoxathiole 3,3-dioxides

243rd National Meeting (2012)

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