3173-53-3Relevant articles and documents
Free-Radical Halogenations. 5. Reaction of Chlorosulfonyl Isocyanate with Alkanes
Mosher, Melvyn W.
, p. 1875 - 1879 (1982)
The free-radical chain reactions of chlorosulfonyl isocyanate with alkanes can be initiated with either light or thermal initiators.The major products in these reactions are chlorides, with low yields of isocyanates and sulfonyl chlorides.On the basis of tertiary to primary hydrogen selectivity of about 120:1 and the relative reactivities of various substrates toward the abstracting radical from chlorosulfonyl isocyanate, the hydrogen-abstracting radical is suggested to be the NCO radical.
POLYMERIZATION, OXYGENATION AND ISOMERIZATION OF ISOCYANIDES UNDER IRRADIATION
Boyer, Joseph H.,Ramakrishnan, V. T.,Srinivasan, K. G.,Spak, A. J.
, p. 43 - 46 (1981)
Irradiation in the presence of triplet oxygen polymerized both 2,4-dimethoxyphenyl and cyclohexyl isocyanide and photoautoxidized each into the corresponding isocyanate.The aryl, but not the alicyclic, isocyanide also photoisomerized into a cyanide.The consumption of an isocyanide was enhanced in the presence of certain aromatic hydrocarbons, e. g., naphthalene and phenanthrene, but was diminished in the presence of pyrene.Two bisisocyanides were unaffected by the presence of oxygen during irradiation.
Supporting-Electrolyte-Free Anodic Oxidation of Oxamic Acids into Isocyanates: An Expedient Way to Access Ureas, Carbamates, and Thiocarbamates
Petti, Alessia,Fagnan, Corentin,van Melis, Carlo G. W.,Tanbouza, Nour,Garcia, Anthony D.,Mastrodonato, Andrea,Leech, Matthew C.,Goodall, Iain C. A.,Dobbs, Adrian P.,Ollevier, Thierry,Lam, Kevin
supporting information, p. 2614 - 2621 (2021/06/27)
We report a new electrochemical supporting-electrolyte-free method for synthesizing ureas, carbamates, and thiocarbamates via the oxidation of oxamic acids. This simple, practical, and phosgene-free route includes the generation of an isocyanate intermediate in situ via anodic decarboxylation of an oxamic acid in the presence of an organic base, followed by the one-pot addition of suitable nucleophiles to afford the corresponding ureas, carbamates, and thiocarbamates. This procedure is applicable to different amines, alcohols, and thiols. Furthermore, when single-pass continuous electrochemical flow conditions were used and this reaction was run in a carbon graphite Cgr/Cgr flow cell, urea compounds could be obtained in high yields within a residence time of 6 min, unlocking access to substrates that were inaccessible under batch conditions while being easily scalable.
Practical one-pot amidation of N -Alloc-, N -Boc-, and N -Cbz protected amines under mild conditions
Hong, Wan Pyo,Tran, Van Hieu,Kim, Hee-Kwon
, p. 15890 - 15895 (2021/05/19)
A facile one-pot synthesis of amides from N-Alloc-, N-Boc-, and N-Cbz-protected amines has been described. The reactions involve the use of isocyanate intermediates, which are generated in situ in the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, to react with Grignard reagents to produce the corresponding amides. Using this reaction protocol, a variety of N-Alloc-, N-Boc-, and N-Cbz-protected aliphatic amines and aryl amines were efficiently converted to amides with high yields. This method is highly effective for the synthesis of amides and offers a promising approach for facile amidation.