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Volumn 46, Issue 48, 2005, Pages 8351-8354

TiCl3/PhN2+-mediated radical addition of ethers to aldimines generated in situ under aqueous conditions

Author keywords

Aldimines; One electron reduction; Radical addition; Three component reaction; Titanium trichloride

Indexed keywords

ALDEHYDE DERIVATIVE; BENZENE DERIVATIVE; CATION; CHLORIDE; ETHER DERIVATIVE; FORMALDEHYDE; HYDROGEN; IMINE; RADICAL; TITANIUM DERIVATIVE;

EID: 27644539170     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.09.158     Document Type: Article
Times cited : (24)

References (30)
  • 2
    • 23044503907 scopus 로고    scopus 로고
    • For inter- and intramolecular radical addition to CN bonds, see: G.K. Friestad Eur. J. Org. Chem. 2005 3157 3172
    • (2005) Eur. J. Org. Chem. , pp. 3157-3172
    • Friestad, G.K.1
  • 23
    • 27644511109 scopus 로고    scopus 로고
    • note
    • 3 solution (30% in 2 N HCl) gave poor yield of 3a because protonation of the amine hampers its condensation with an aldehyde.
  • 24
    • 0000573083 scopus 로고
    • 2CHN group easily undergoes aldol type condensation and polymers are usually formed. E.C. Wagner J. Org. Chem. 19 1954 1862 1881
    • (1954) J. Org. Chem. , vol.19 , pp. 1862-1881
    • Wagner, E.C.1
  • 25
    • 27644495740 scopus 로고    scopus 로고
    • note
    • We found (see Ref. 5) that tert-butyl radical, owing to steric hindrance, failed to undergo imine addition. Thus, radical addition to the CN bond is sensitive to the steric hindrance of either the radical or the imine C-atom. This sensitivity is in line with a crowded transition state due to Ti(IV) complexation rather than to imine protonation.
  • 27
    • 27644575100 scopus 로고    scopus 로고
    • note
    • β-H atom abstraction form THF generates the β-ethereal radical responsible for the formation of 4a-e.
  • 30
    • 27644481679 scopus 로고    scopus 로고
    • note
    • 2O), thus the equilibrium may well be shifted towards iminium radical B, at pH ≈ 1.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.