866483-65-0Relevant articles and documents
An efficient method for the preparation of N-alkylamides from alkyl diphenylphosphinites and amides by using methyl acrylate
Aoki, Hidenori,Mukaiyama, Teruaki
, p. 456 - 457 (2006)
N,N-Dibenzyltrifluoroacetamide was formed in good yield by treating benzyl diphenylphosphinite with N-benzyltrifluoroacetamide in the presence of easily available methyl acrylate under mild conditions. Yields obtained for the corresponding inverted sulfon
Camphorquinone: A new and efficient oxidant for the preparation of 2-thio-substituted benzothiazoles from alcohols by oxidation-reduction condensation
Pluempanupat, Wanchai,Temyarasilp, Parinthorn,Widhalm, Michael,Chavasiri, Warinthorn
, p. 418 - 430 (2014/06/10)
A convenient one-pot procedure for the preparation of various 2-thio-substituted benzothiazoles from alcohols and benzothiazole-2-thiol utilizing camphorquinone-mediated oxidation-reduction condensation is disclosed. The condensation between benzothiazole-2-thiol and alkyl diphenylphosphinites, generated in situ from alcohols and chlorodiphenylphosphine, proceeded smoothly in the presence of camphorquinone to furnish the corresponding benzothiazoles in good to moderate yields.
Cyanation of alcohols with diethyl cyanophosphonate and 2,6-dimethyl-1,4-benzoquinone by a new type of oxidation-reduction condensation
Masutani, Kouta,Minowa, Tomofumi,Hagiwara, Yoshiaki,Mukaiyama, Teruaki
, p. 1106 - 1117 (2007/10/03)
Cyanation of various alcohols by a new type of oxidation-reduction condensation is described. Primary alkyl diphenylphosphinites, 2,6-dimethyl-1,4-benzoquinone (DMBQ), and diethyl cyanophosphonate gave the corresponding nitriles in high yields. During the above experiment on cyanation of 4-phenylbutan-2-ol, the unexpected formation of a mixture of nitrile and isocyanide was observed. After careful examination of the reaction conditions, selective synthesis of isocyanides from secondary alcohols was successfully accomplished by the use of zinc oxide (ZnO) as an additive. Reaction of tertiary alcohols provided the corresponding isocyanides exclusively in the absence of an additive. Cyanation of optically active alcohols was tried in order to clarify the stereochemistry of this reaction, and the reaction was thus proved to proceed with the inversion of configuration.
Selective synthesis of isocyanides from secondary alcohols by a new type of oxidation-reduction condensation
Masutani, Kouta,Minowa, Tomofumi,Mukaiyama, Teruaki
, p. 1124 - 1125 (2007/10/03)
Selective synthesis of isocyanides from secondary alcohols via alkyl diphenylphosphinites is established by a new type of oxidation-reduction condensation in controlling the ambident reactivity of cyanide anion. In the presence of ZnO, isocyanides are obtained exclusively in moderate to high yields. Copyright
