Bromination of hydrocarbons with CBr₄, initiated by light-emitting diode irradiation

• Yuta Nishina,
• Bunsho Ohtani and
• Kotaro Kikushima

Beilstein J. Org. Chem. 2013, 9, 1663–1667, doi:10.3762/bjoc.9.190

•  1, entry 9), showing that the present reaction was a radical reaction. Based on the assumption that the initial formation of bromine radicals would be important, addition of catalytic amounts of CBr4 along with various bromination sources was examined (Table 1, entries 10–12). The combination of

Computational study of the rate constants and free energies of intramolecular radical addition to substituted anilines

• Andreas Gansäuer,
• Meriam Seddiqzai,
• Tobias Dahmen,
• Rebecca Sure and
• Stefan Grimme

Beilstein J. Org. Chem. 2013, 9, 1620–1629, doi:10.3762/bjoc.9.185

• indanes or dihydrobenzofurans are too slow to be useful synthetically. Keywords: aromatic substitution; computational chemistry; DFT-D3; free radical; polar effects; radical reaction; Introduction The development of efficient catalytic reactions is one of the central issues of chemistry [1][2]. Radical

• our system and that are experimentally well investigated. An ideal radical reaction in this respect is the 5-exo cyclization (Scheme 2) of the 5-hexenyl radical. The reaction is preparatively highly important and has been used in many syntheses of complex molecules [3][4][5]. Moreover, the kinetics of

Diastereoselective radical addition to γ-alkyl-α-methylene-γ-butyrolactams and the synthesis of a chiral pyroglutamic acid derivative

• Tomoko Yajima,
• Eriko Yoshida and
• Masako Hamano

Beilstein J. Org. Chem. 2013, 9, 1432–1436, doi:10.3762/bjoc.9.161

• the reaction were also revealed. This stereoselective radical reaction was used for synthesis of chiral pyroglutamic acid derivatives starting from a commercially available chiral amino acid. Keywords: chelation controlled reaction; diastereoselective reaction; free radical; lactams; pyroglutamic

Cascade radical reaction of substrates with a carbon–carbon triple bond as a radical acceptor

• Hideto Miyabe,
• Ryuta Asada and
• Yoshiji Takemoto

Beilstein J. Org. Chem. 2013, 9, 1148–1155, doi:10.3762/bjoc.9.128

• 2002 that hydroxamic acid derivatives are useful achiral templates in enantioselective Diels–Alder reactions [69][70]. To study the effect of hydroxamate ester as an achiral template in the intermolecular radical reaction, our experiments began with the investigation of cascade radical addition

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