Photoinduced synthesis of unsymmetrical diaryl selenides from triarylbismuthines and diaryl diselenides

• Yohsuke Kobiki,
• Shin-ichi Kawaguchi,
• Takashi Ohe and
• Akiya Ogawa

Beilstein J. Org. Chem. 2013, 9, 1141–1147, doi:10.3762/bjoc.9.127

• ). In 1999, Barton and co-workers reported that diaryl selenide was obtained by the reaction of triarylbismuthine with diphenyl diselenide under heating at high temperature (140 °C) [65], but the photoinduced reaction was not investigated. In this letter, we will report the radical reaction of diaryl

• a bed of celite (Celite 535). The crude product was purified by preparative TLC on silica gel (eluent: hexane/EtOAc). Details about compounds 3ab [30], 3ac [14], 3ad [17], 3ba [17], 3bb [31], 3ca [17], 3da [32], 3ea [28] and 3dc [30] were reported in the corresponding articles. Photoinduced radical

• reaction of diaryl diselenide with triphenylbismuthine. Photoinduced reaction of diphenyl disulfide with triphenylbismuthine. A plausible reaction pathway for the photoinduced reaction of diaryl diselenide with triarylbismuthine. Reaction of diphenyl diselenide with triphenylbismuthine under different

Some aspects of radical chemistry in the assembly of complex molecular architectures

• Béatrice Quiclet-Sire and
• Samir Z. Zard

Beilstein J. Org. Chem. 2013, 9, 557–576, doi:10.3762/bjoc.9.61

• through a second radical reaction with dichlorovinyl ethylsulfone (132) [54]. The ethylsulfonyl radical created in the addition–elimination process of intermediate radical 133 fragments to liberate sulfur dioxide and an ethyl radical that is capable of propagating the chain. The resulting product 134