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Volumn 65, Issue 27, 2009, Pages 5278-5283

Diethyl bromodifluoromethylphosphonate: a highly efficient and environmentally benign difluorocarbene precursor

Author keywords

Diethyl bromodifluoromethylphosphonate; Difluorocarbene; Difluoromethylation

Indexed keywords

CARBENOID; CARBONYL DERIVATIVE; DIETHYL BROMODIFLUOROMETHYLPHOSPHONATE; DIFLUOROCARBENE; PHENOL DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; THIOESTER; THIOPHENOL DERIVATIVE; UNCLASSIFIED DRUG;

EID: 66149151773     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.04.082     Document Type: Article
Times cited : (113)

References (43)
  • 2
    • 66149115860 scopus 로고    scopus 로고
    • For comprehensive reviews see
    • For comprehensive reviews see:
  • 23
    • 66149123530 scopus 로고    scopus 로고
    • For difluoromethylation of phenols or thiophenols see selected articles
    • For difluoromethylation of phenols or thiophenols see selected articles:
  • 32
    • 66149121271 scopus 로고    scopus 로고
    • This low cost diethyl bromodifluoromethylphosphonate is supplied by many famous chemical companies. It may be easily prepared by the procedure of Burton and Flynn in excellent yield (>95, using nearly equivalent amounts of triethyl phosphite and dibromofluoromethane a precursor of difluorocarbene itself, Curiously, this version of Michaelis-Arbuzov reaction also involves a difluorocarbene as an unstable intermediate. For the synthesis of diethyl bromodifluoromethylphosphonate see also
    • This low cost diethyl bromodifluoromethylphosphonate is supplied by many famous chemical companies. It may be easily prepared by the procedure of Burton and Flynn in excellent yield (>95%), using nearly equivalent amounts of triethyl phosphite and dibromofluoromethane (a precursor of difluorocarbene itself). Curiously, this version of Michaelis-Arbuzov reaction also involves a difluorocarbene as an unstable intermediate. For the synthesis of diethyl bromodifluoromethylphosphonate see also:
  • 35
    • 58149312985 scopus 로고    scopus 로고
    • 3 supports reveals that they are chemically different as function of their preparation conditions. See:
    • 3 supports reveals that they are chemically different as function of their preparation conditions. See:. Gershonov E., Columbus I., and Zafrani Y. J. Org. Chem. 74 (2009) 329
    • (2009) J. Org. Chem. , vol.74 , pp. 329
    • Gershonov, E.1    Columbus, I.2    Zafrani, Y.3
  • 39
    • 66149121683 scopus 로고    scopus 로고
    • note
    • In the hydrolysis of difluorocarbene, the hydroxide ion initially reacts with this unstable intermediate to form difluoromethanol, which eventually undergoes an elimination of HF followed by further hydrolysis to give fluoride and formate salts.{A figure is presented}


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.