메뉴 건너뛰기




Volumn 121, Issue 23, 1999, Pages 5444-5449

1,2-shifts of hydrogen atoms in aryl radicals

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RADICAL;

EID: 0033575097     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja984472d     Document Type: Article
Times cited : (58)

References (59)
  • 1
    • 0003792563 scopus 로고
    • Elsevier: New York
    • For a review on 1,2-shifts in carbocations, see: Vogel, P. Carbocation Chemistry; Elsevier: New York, 1985; pp 323-372.
    • (1985) Carbocation Chemistry , pp. 323-372
    • Vogel, P.1
  • 4
    • 0000108509 scopus 로고
    • Kochi, J. K., Ed.; Wiley: New York
    • For a review on 1,2-shifts in radicals, see: Wilt, J. W. Free Radicals; Kochi, J. K., Ed.; Wiley: New York, 1973; Vol. I., p 333-501.
    • (1973) Free Radicals , vol.1 , pp. 333-501
    • Wilt, J.W.1
  • 5
    • 0003928702 scopus 로고
    • Cambridge University Press: London
    • See also: Nonhebel; Walton Free-Radical Chemistry; Cambridge University Press: London, 1974; pp 498-552.
    • (1974) Free-Radical Chemistry , pp. 498-552
    • Nonhebel1    Walton2
  • 7
    • 0001825245 scopus 로고
    • de Mayo, P., Ed.; Wiley: New York
    • For a review on 1,2-shifts in carbanions, see: Zimmerman, H. E. Molecular Rearrangements, Part 1; de Mayo, P., Ed.; Wiley: New York, 1963; p 345.
    • (1963) Molecular Rearrangements , Issue.1 PART , pp. 345
    • Zimmerman, H.E.1
  • 12
    • 0000102616 scopus 로고
    • See also: Pine, S. H. Org. React. 1970, 18, 403-464.
    • (1970) Org. React. , vol.18 , pp. 403-464
    • Pine, S.H.1
  • 13
    • 0002890057 scopus 로고
    • For a review on the Wittig rearrangement, see: Johnstone, R. A. W. Mech. Mol. Migr. 1969, 2, 249-266.
    • (1969) Mech. Mol. Migr. , vol.2 , pp. 249-266
    • Johnstone, R.A.W.1
  • 14
    • 0345308959 scopus 로고    scopus 로고
    • For reviews on neophyl rearrangements, see refs 4-6
    • For reviews on neophyl rearrangements, see refs 4-6.
  • 19
    • 0344877788 scopus 로고    scopus 로고
    • note
    • BP/DN** calculations were performed using the density functional program implemented in the Spartan 5.0 software package (Wavefunction, Inc., Irvine, CA 92612). Vibrational analyses at the BP/DN** level of theory have confirmed that the transition-state species reported here are characterized by one and only one imaginary vibrational frequency and that species corresponding to energy minima have no imaginary vibrational frequencies.
  • 20
    • 0030559308 scopus 로고    scopus 로고
    • Coupled cluster ab initio calculations corrected for electron correlation, using Dunning's triple-ζ polarization basis set (CCSD(T)/TZ2P), as implemented in the ACES II program, give an activation energy of "at least 47 kcal/mol" for the 1,2-shift of hydrogen in vinyl radical and a dissociation threshold of 40.7 kcal/mol for the β-scission of vinyl radical to acetylene and a hydrogen atom: Wang, J.-H.; Chang, H.-C; Chen, Y.-T. Chem. Phys. 1996, 206, 43-56.
    • (1996) Chem. Phys. , vol.206 , pp. 43-56
    • Wang, J.-H.1    Chang, H.-C.2    Chen, Y.-T.3
  • 21
    • 0344877785 scopus 로고
    • The only prior calculations we have found for the 1,2-shift of hydrogen in phenyl radical, although now quite out of date, also predicted a high energy barrier: Burmistrov, V. N.; Khudyakov, I. V.; Christensen, A. Izv. Akad Nauk. Ser. Khim. 1979, 460-2 (Chem. Abstr. No. 90:186104).
    • (1979) Izv. Akad Nauk. Ser. Khim. , pp. 460-462
    • Burmistrov, V.N.1    Khudyakov, I.V.2    Christensen, A.3
  • 22
    • 0345308957 scopus 로고    scopus 로고
    • The only prior calculations we have found for the 1,2-shift of hydrogen in phenyl radical, although now quite out of date, also predicted a high energy barrier: Burmistrov, V. N.; Khudyakov, I. V.; Christensen, A. Izv. Akad Nauk. Ser. Khim. 1979, 460-2 (Chem. Abstr. No. 90:186104).
    • Chem. Abstr. , vol.90 , pp. 186104
  • 24
    • 0013587923 scopus 로고    scopus 로고
    • Evidence for the migration of hydrogen atoms in dehydrobenzenes (aryl diradicals) at elevated temperatures has been seen in the beautiful work of R. F. C. Brown et al.: Brown, R. F. C.; Eastwood, F. W. Pure Appl. Chem. 1996, 68, 261-266.
    • (1996) Pure Appl. Chem. , vol.68 , pp. 261-266
    • Brown, R.F.C.1    Eastwood, F.W.2
  • 28
    • 0345308951 scopus 로고    scopus 로고
    • note
    • 16
  • 36
    • 33947443787 scopus 로고
    • Modification of the method by Hass, H. B.; Bender, M. L. J. Am. Chem. Soc. 1949, 71, 1767-1769.
    • (1949) J. Am. Chem. Soc. , vol.71 , pp. 1767-1769
    • Bender, M.L.1
  • 37
    • 0005549715 scopus 로고
    • Rabjohn, N., Ed.
    • See also: Hass, H. B.; Bender, M. L. In Organic Syntheses; Rabjohn, N., Ed.; 1963, Collect. Vol. 4, pp 932-934.
    • (1963) Organic Syntheses , vol.4 , pp. 932-934
    • Hass, H.B.1    Bender, M.L.2
  • 55
    • 0344877770 scopus 로고    scopus 로고
    • Purchased from Aldrich Chemical Co., Milwaukee, WI
    • Purchased from Aldrich Chemical Co., Milwaukee, WI.
  • 56
    • 0344014691 scopus 로고    scopus 로고
    • note
    • The ultraviolet light that causes photocyclization also interconverts the (E)- and (Z)-stilbene isomers; therefore, either isomer (or a mixture of isomers) can be used for the photochemical ring closure.
  • 58
    • 0345308942 scopus 로고    scopus 로고
    • note
    • Yield of purified mixture (%) after separation from higher molecular weight byproducts by flash vacuum chromatography.
  • 59
    • 0344445998 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra of the purified mixture of monomeric products.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.