820961-79-3Relevant articles and documents
Conversion of tertiary alcohols to tert-alkyl azides by way of quinone-mediated oxidation-reduction condensation using alkyl diphenylphosphinites
Kuroda, Kiichi,Hayashi, Yujiro,Mukaiyama, Teruaki
, p. 6358 - 6364 (2007)
A novel method for the preparation of alkyl azides from alcohols by way of oxidation-reduction condensation is described. In this reaction, the sterically-hindered tert-alkyl phosphinites that are prepared from the corresponding alcohols are converted int
Stereospecific C-S bond formation from chiral tertiary alcohols by quinone-mediated oxidation-reduction condensation using alkyl diphenylphosphinites and its application to the synthesis of a chiral tertiary thiol
Ikegai, Kazuhiro,Pluempanupat, Wanchai,Mukaiyama, Teruaki
, p. 780 - 790 (2007/10/03)
Oxidation-reduction condensation between 2-sulfanyl-1,3-benzothiazole (Btz-SH) and the alkyl diphenylphosphinites 1, prepared from tertiary alcohols, proceeded smoothly in the presence of 2,6-di-t-butyl-1,4-benzoquinone (DBBQ) and the corresponding S-alky
A convenient method for the synthesis of dialkyl ethers by alkylation of alcohols using phosphinimidates in the presence of a catalytic amount of trimethylsilyl triflate
Aoki, Hidenori,Mukaiyama, Teruaki
, p. 1255 - 1264 (2007/10/03)
An alkylation reaction of alcohols with alkyl N-(methylsulfonyl) diphenylphosphinimidates proceeded smoothly in the presence of a catalytic amount of trimethylsilyl triflate (Me3SiOTf) in DME at room temperature and the corresponding ethers were afforded in good to high yields. An alkyl N-(methylsulfonyl)diphenylphosphinimidate can be prepared easily from an alkyl diphenylphosphinite and methanesulfonyl azide, and is isolated without tedious operation. Moreover, it is easy to handle and can be stored for several months at room temperature because of its air- and moisture-resistant character. Also, one-pot tertiary alkylations of alcohols by using t-alkyl diphenylphosphinites and diphenoxyphosphoryl azide proceeded efficiently in the presence of a catalytic amount of Me3SiOTf in cyclohexane/CH 2Cl2 at 0°C or -10°C, and gave the corresponding tertiary alkyl ethers in good yields. By following these methods, various ethers having alkali-sensitive functional groups can be prepared easily.
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.
Preparation of tert-Alkyl aryl sulfides from tert-alcohols via quinone-mediated oxidation-reduction condensation between tert-Alkyl diphenylphosphinites and 2-sulfanyl-1,3-benzothiazole
Ikegai, Kazuhiro,Pluempanupat, Wanchai,Mukaiyama, Teruaki
, p. 638 - 639 (2007/10/03)
A convenient two-step procedure for the construction of sulfur-containing quaternary centers from tert-alcohols involving chiral ones is established. tert-Alkyl diphenylphosphinites 1 were easily prepared in excellent yields from tert-alcohols and ClPPhs
