메뉴 건너뛰기




Volumn 118, Issue 25, 1996, Pages 5952-5960

Side-chain fragmentation of arylalkanol radical cations. Carbon-carbon and carbon-hydrogen bond cleavage and the role of α- and β-OH groups

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL;

EID: 0030038685     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja954236s     Document Type: Article
Times cited : (67)

References (56)
  • 7
    • 0003213467 scopus 로고
    • and references therein
    • Maslak, P. Top. Curr. Chem. 1993, 168, 1-46 and references therein.
    • (1993) Top. Curr. Chem. , vol.168 , pp. 1-46
    • Maslak, P.1
  • 14
    • 0001544762 scopus 로고
    • Dinnocenzo, J. P.; Todd, W. P.; Simpson, T. R.; Gould, I. R. J. Am. Chem. Soc. 1990, 112, 2462-2464. Shaik, S. S.; Dinnocenzo, J. P. J. Org. Chem. 1990, 55, 3434-3436.
    • (1990) J. Org. Chem. , vol.55 , pp. 3434-3436
    • Shaik, S.S.1    Dinnocenzo, J.P.2
  • 18
    • 0004186505 scopus 로고
    • Fox, M. A., Chanon, M., Eds.; Elsevier: Amsterdam
    • Ci, X.; Whitten, D. G. Photoinduced Electron Transfer; Fox, M. A., Chanon, M., Eds.; Elsevier: Amsterdam, 1988; Part C, p 553.
    • (1988) Photoinduced Electron Transfer , Issue.100 PART , pp. 553
    • Ci, X.1    Whitten, D.G.2
  • 26
    • 8944248298 scopus 로고    scopus 로고
    • note
    • 2+ with other anisole derivatives (see ref 24).
  • 27
    • 0000537422 scopus 로고
    • •- both the methoxylated and the non-methoxylated ring are expected to be attacked (on the basis of the rate constants for reaction with anisole and benzene see ref 24 and: Neta, P.; Madhavan, V.; Zemel, H.; Fessenden, R. W. J. Am. Chem. Soc. 1977, 99, 163-154. If this occurs, the equality of the yields from reaction with (a) the selective and (b) the nonselective oxidant indicates rapid intramolecular electron transfer from the methoxylated to the "electron hole" at the non-methoxylated ring.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 163-1154
    • Neta, P.1    Madhavan, V.2    Zemel, H.3    Fessenden, R.W.4
  • 28
    • 8944251655 scopus 로고    scopus 로고
    • note
    • In the insets b of Figures 1 and 2 are shown traces reflecting the optical density change at 300 nm in a time range extending to 1.6 ms after generation of the radical cations by reaction described in eq 8.
  • 30
    • 8944247766 scopus 로고    scopus 로고
    • note
    • 3.
  • 33
    • 8944246345 scopus 로고    scopus 로고
    • note
    • 33 Thus, the former group should be more effective than the latter in stabilizing the positive charge which, as already mentioned, should accumulate on the scissile bond in the transition state leading to the cleavage.
  • 38
    • 8944260915 scopus 로고    scopus 로고
    • note
    • •OH.
  • 40
    • 8944243087 scopus 로고    scopus 로고
    • note
    • 42 and moreover we cannot envisage any mechanism by which the charge can be transferred from the aromatic ring to the oxygen atom since there is no direct interaction between the π system and the O-H bond.
  • 51
    • 0003297908 scopus 로고
    • The assignment of the erythro and threo forms for 1-(4-methoxyphenyl)-2-methoxy-l-propanol and its acetate was done by comparison of their NMR data with those of erythro and threo forms of 1,2-disubstituted l-arylpropanes. Barba, I.: Chinchilla, R.; Gomez, C. J. Org. Chem. 1990, 55, 3270-3272.
    • (1990) J. Org. Chem. , vol.55 , pp. 3270-3272
    • Barba, I.1    Chinchilla, R.2    Gomez, C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.