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Volumn 67, Issue 3, 2011, Pages 590-596

PhI(OAc)2-mediated iminobromination for synthesis of bromomethyl cyclic imines starting from alkenyl carbonitriles and Grignard reagents

Author keywords

Alkenyl carbonitriles; Bromomethyl cyclic imines; Grignard reagents; Iminobromination; PhI(OAc)2

Indexed keywords

ALKENYL GROUP; BROMOMETHYL CYCLIC IMINE; CYANIDE; NUCLEOPHILE; UNCLASSIFIED DRUG;

EID: 78650515875     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.11.060     Document Type: Article
Times cited : (9)

References (36)
  • 4
    • 78650510344 scopus 로고    scopus 로고
    • For reviews
    • For reviews, see:
  • 8
    • 78650514585 scopus 로고    scopus 로고
    • For prior studies on iminobromination using NBS
    • For prior studies on iminobromination using NBS, see:
  • 16
    • 78650513268 scopus 로고    scopus 로고
    • 2-mediated oxidative functionalization of alkenes
    • 2-mediated oxidative functionalization of alkenes, see:
  • 25
    • 78650513025 scopus 로고    scopus 로고
    • When PhMgCl was utilized with carbonitrile 1a under the present reaction conditions, the desired chloromethyl dihydropyrrole 4aa-Cl was obtained in only 41% yield
    • When PhMgCl was utilized with carbonitrile 1a under the present reaction conditions, the desired chloromethyl dihydropyrrole 4aa-Cl was obtained in only 41% yield.
  • 26
    • 78650513492 scopus 로고    scopus 로고
    • Tetrahydropyridine 6 was found to be very unstable and decompose to a complex mixture at room temperature
    • Tetrahydropyridine 6 was found to be very unstable and decompose to a complex mixture at room temperature.
  • 27
    • 78650515140 scopus 로고    scopus 로고
    • Brominated N-H imine 7 might be formed via allylic radical bromination, although we are not certain as to the detailed reaction course. For example, it is speculated that formation of N-bromoimine followed by its thermal hemolytic cleavage could generate iminyl and bromine radicals as shown below. 1,5-Hydrogen shift by radical abstraction of the allylic hydrogen with the iminyl radical could afford the allylic radical that could be trapped by the resulting bromine radical to give 7
    • Brominated N-H imine 7 might be formed via allylic radical bromination, although we are not certain as to the detailed reaction course. For example, it is speculated that formation of N-bromoimine followed by its thermal hemolytic cleavage could generate iminyl and bromine radicals as shown below. 1,5-Hydrogen shift by radical abstraction of the allylic hydrogen with the iminyl radical could afford the allylic radical that could be trapped by the resulting bromine radical to give 7.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.