87671-54-3Relevant academic research and scientific papers
Synthesis of trifluoromethylated compounds from alcohols via alkoxydiphenylphosphines
Li, Jun-Li,Yang, Xian-Jin,Wang, Yanan,Liu, Jin-Tao
, p. 254 - 259 (2015)
The transformation of hydroxyl group in benzyl or allyl alcohols to trifluoromethyl was achieved via the reaction of the corresponding alkyloxydiphenylphosphine and CuCF3, generated in situ from methyl fluorosulfonyldifluoroacetate and CuI, under mild conditions. A plausible mechanism was proposed on the basis of experimental results.
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 nitriles from primary alcohols by a new type of oxidation-reduction condensation using 2,6-dimethyl-1,4-benzoquinone and diethyl cyanophosphonate
Mukaiyama, Teruaki,Masutani, Kouta,Hagiwara, Yoshiaki
, p. 1192 - 1193 (2007/10/03)
Cyanation of alkoxydiphenylphosphines, in situ prepared from nBuLi and various primary alcohols, with 2,6-dimethyl-1,4- benzoquinone (DMBQ) and diethyl cyanophosphonate provided the corresponding nitriles in high yields.
The Reactivity of Organophosphorus Compounds. Part 35. Pyrolysis of 3-Aryl- and 3-Alkyl-2,3-dihydro-1,3,2-benzoxazaphosph(V)oles
Cadogan, J. I. G.,Husband, James B.,McNab, Hamish
, p. 1489 - 1495 (2007/10/02)
Pyrolysis of 2,2-diphenyl-2-methoxy derivatives of the title compounds in the gas phase gives phosphinates or phosphinamidates derived from the substrate by formal loss of methylene.Control experiments show that the reaction involves radical cleavage initiated by rupture of the oxazaphosph(V)ole ring.Pyrolysis of 3-aryl-2,2-dimethoxy-2-phenyl derivatives of the title compounds under similar conditions results in the formation of 3-aryl-2,3-dihydro-2-oxo-2-phenyl-1,3,2-benzoxazaphospholes.No significant products could be isolated from 2,2,2-trimethoxy derivatives, though vigorous conditions were required for their complete breakdown.The pyrolysis of the corresponding 2,2-diphenyl-2-ethoxy, 2,2-diethoxy-2-phenyl, and 2,2,2-triethoxy compounds gave higher yields of similar products, possibly via a six-centre concerted elimination.
