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DOI: 10.1039/A907574G (Paper) Reference Section for: J. Chem. Soc., Dalton Trans., 1999, 4397-4406

Ring opening reactions of thiiranes by alkoxo- and aryloxo-gold(I) complexes

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Yoko Usui, Junko Noma, Masafumi Hirano and Sanshiro Komiya

Abstract

Alkoxo- and aryloxo-gold(I) complexes [Au(OR)L] [R = CH(CF3)2, L = PPh3 1a or PCy3 1b; R = Ph, L = PPh3 1c, PCy3 1d or PMe3 1e] smoothly reacted with ethylene sulfide to give the corresponding 2-(alkoxy- or -aryloxy)ethylsulfanylgold(I) complexes [Au(SCH2CH2OR)L] 2 at room temperature. Similar treatments of 1a–1e with propylene sulfide, isobutylene sulfide, or styrene sulfide selectively cleaved the less hindered C–S bond of thiiranes to give corresponding 2-(alkoxy- or -aryloxy)ethylsulfanylgold(I) complexes. Reactions of 1a with cis- and trans-2-butene sulfide gave syn- and anti-[Au(SCHMeCHMeOR)L], respectively, suggesting a mechanism involving an SN2 type trans addition of alkoxogold(I) complexes toward thiiranes.

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