- Generation and cyclization of unsaturated carbamoyl radicals derived from S-4-pentynyl carbamothioates under tin-free conditions
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The radical reaction of benzenethiol with S-4-pentynyl carbamothioates provides a valuable protocol for the tin-free generation of carbamoyl radicals, which arise from intramolecular substitution at sulfur by the initial sulfanylvinyl radicals. This procedure can be usefully employed to achieve N-benzylcarbamoyl radical 5-exo and 4-exo cyclizations leading, respectively, to pyrrolidinones and azetidinones, although, for the latter, it seems of lesser utility. Novel evidence is presented that. N-tosyl-substituted carbamoyl radicals display a peculiar tendency to yield the corresponding isocyanate by β-elimination of the tosyl radical.
- Benati, Luisa,Bencivenni, Giorgio,Leardini, Rino,Minozzi, Matteo,Nanni, Daniele,Scialpi, Rosanna,Spagnolo, Piero,Zanardi, Giuseppe
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- Regioselective palladium-catalyzed intramolecular oxidative aminofluorination of unactivated alkenes
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A novel Pd-catalyzed regioselective intramolecular aminofluorination of unactivated alkenes has been developed, which is an efficient method for the synthesis of a variety of monofluoromethylated nitrogen-containing heterocycles.
- Wu, Tao,Cheng, Jiashun,Chen, Pinhong,Liu, Guosheng
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supporting information
p. 8707 - 8709
(2013/09/23)
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- Dithiocarbamate group transfer cyclization reactions of carbamoyl radicals under "tin-free" conditions
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Oxygen or nitrogen? Radical chemists overwhelmingly choose to work with xanthates rather than dithiocarbamates, yet the latter offer a distinct advantage in the case of a new method for generating carbamoyl radicals. Functionalized lactams of various ring
- Grainger, Richard S.,Innocenti, Paolo
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p. 3445 - 3448
(2007/10/03)
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