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Volumn 61, Issue 20, 1996, Pages 7040-7044

Substituent effects on the photocleavage of benzyl-sulfur bonds. Observation of the "Meta effect"

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Indexed keywords


EID: 0000441041     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9606923     Document Type: Article
Times cited : (27)

References (88)
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    • (1983) Organic Photochemistry , vol.6
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    • note
    • In general as solvent nucleophilicity increases and radical abstractability decreases, photosolvolysis products are formed.
  • 6
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    • note
    • Photofugacity refers to the rate of leaving group dissociation from the excited state. For a discussion, see ref 7h.
  • 8
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    • note
    • Some counterions have been shown to reduce intermediate radical or ionic pairs. For an example, see ref 19b.
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    • M.S. Thesis, Brigham Young University
    • (g) Michelsen, R. M.S. Thesis, Brigham Young University, 1991.
    • (1991)
    • Michelsen, R.1
  • 66
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    • For a recent example of time-esolved studies on benzyl halide photocleavage, see: McGowan, W. M.; Hilinski, E. F. J. Am. Chem. Soc. 1995, 117, 9019.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 9019
    • McGowan, W.M.1    Hilinski, E.F.2
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    • Personal communication
    • Personal communication with P. J. Wedge.
    • Wedge, P.J.1
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    • a Scale Based Upon Spin Delocalization
    • Viehe, H. G., Janousek, Z., Merenyi, R., Eds.; D. Reidel: Dordrecht
    • a Scale Based Upon Spin Delocalization. In Substituent Effects in Radical Chemistry; Viehe, H. G., Janousek, Z., Merenyi, R., Eds.; D. Reidel: Dordrecht, 1986; pp 171-188.
    • (1986) Substituent Effects in Radical Chemistry , pp. 171-188
    • Arnold, D.R.1
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    • . Revisited
    • Viehe, H. G., Janousek, Z., Merenyi, R., Eds.; D. Reidel: Dordrecht
    • . Revisited. In Substituent Effects in Radical Chemistry; Viehe, H. G., Janousek, Z., Merenyi, R., Eds.; D. Reidel: Dordrecht, 1986; pp 325-328.
    • (1986) Substituent Effects in Radical Chemistry , pp. 325-328
    • Jackson, R.A.1
  • 79
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    • 7f,h It has been suggested that a better method for determining reaction multiplicity in benzyl-heteroatom photocleavages is to use the naphthyl system instead of benzyl. Among the substituents we studied, it is likely that the nitro (1j and 1k) and perhaps the cyano (1h and 1i) involve a triplet excited state. See: Blakemore, D. C.; Gilbert, A. J. Chem. Soc., Perkin Trans. 1 1992, 16, 2265. For a recent example of excited state multiplicity playing a role in homolytic vs heterolytic cleavages, see: Jiménez, M. C.; Miranda, M. A.; Tormos, R. Heterocycles 1996, 43, 339.
    • (1992) J. Chem. Soc., Perkin Trans. 1 , vol.16 , pp. 2265
    • Blakemore, D.C.1    Gilbert, A.2
  • 80
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    • 7f,h It has been suggested that a better method for determining reaction multiplicity in benzyl-heteroatom photocleavages is to use the naphthyl system instead of benzyl. Among the substituents we studied, it is likely that the nitro (1j and 1k) and perhaps the cyano (1h and 1i) involve a triplet excited state. See: Blakemore, D. C.; Gilbert, A. J. Chem. Soc., Perkin Trans. 1 1992, 16, 2265. For a recent example of excited state multiplicity playing a role in homolytic vs heterolytic cleavages, see: Jiménez, M. C.; Miranda, M. A.; Tormos, R. Heterocycles 1996, 43, 339.
    • (1996) Heterocycles , vol.43 , pp. 339
    • Jiménez, M.C.1    Miranda, M.A.2    Tormos, R.3
  • 81
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    • note
    • CACheMOPAC version 94 with multiplicity = singlet, parameter = AM1, and CI level = 2; CAChe Scientific, Inc.
  • 88
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    • note
    • Nitrogen was purified by being passed through an Ace-Burlitch inert atmosphere system containing a column packed with a BASF R3-11 catalyst followed by another column packed with Aquasorb drying agent.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.