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Volumn 22, Issue 4, 2009, Pages 265-273

Ionic and radical fragmentations of alkoxyhalocarbenes - a perspective

Author keywords

Carbenes; Carbocations; Ion pairs; Radicals

Indexed keywords

ACTIVATION PARAMETER; CARBENE; CARBENES; CARBOCATION; CARBOCATIONS; CRYOGENIC MATRICES; CYCLOPROPYL; GASPHASE; ION PAIRS; LASER FLASH PHOTOLYSIS; NON-POLAR SOLVENTS; ORDERS OF MAGNITUDE; POLAR SOLVENTS; RADICAL FRAGMENTATION; RADICALS;

EID: 65949091142     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1471     Document Type: Review
Times cited : (8)

References (60)
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    • W. H. Saunders, Jr., R. H. Paine, J. Am. Chem. Soc. 1961, 83, 882-885. The formolysis of neophyl tosylate was carried out in boiling formic acid (∼100°C). If the observed product ratios were corrected to 25 °C, the temperature of the carbene fragmentations, there would presumably be an even greater product selectivity of formolysis versus fragmentation.
    • W. H. Saunders, Jr., R. H. Paine, J. Am. Chem. Soc. 1961, 83, 882-885. The formolysis of neophyl tosylate was carried out in boiling formic acid (∼100°C). If the observed product ratios were corrected to 25 °C, the temperature of the carbene fragmentations, there would presumably be an even greater product selectivity of formolysis versus fragmentation.
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    • The substitution products from 38 and 39 are menthol and neomenthol
    • H. Feltkamp, F. Koch, T. N. Thanh, Annalen 1967, 707, 95-99. The substitution products from 38 and 39 are menthol and neomenthol.
    • (1967) Annalen , vol.707 , pp. 95-99
    • Feltkamp, H.1    Koch, F.2    Thanh, T.N.3
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    • For leading references, see notes 3 and 4 in reference 28
    • For leading references, see notes 3 and 4 in reference 28.
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    • See the discussion and citations in reference 19, 463-478
    • See the discussion and citations in reference 19, 463-478.
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    • For examples of ROCCl isomers, see M. A. Kesselmayer, R. S. Sheridan, J. Am. Chem. Soc. 1986, 108, 99-107; 844-845
    • For examples of ROCCl isomers, see M. A. Kesselmayer, R. S. Sheridan, J. Am. Chem. Soc. 1986, 108, 99-107; 844-845.
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    • The cations of ion pairs 59 and 60 are very likely delocalized (i.e., 52); only exo-2-norbornyl methyl ether is formed; see reference 28.
    • The cations of ion pairs 59 and 60 are very likely delocalized (i.e., 52); only exo-2-norbornyl methyl ether is formed; see reference 28.
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    • For a recent discussion of the electronic structure of the cyclopro-pylcarbinyl cation, see
    • For a recent discussion of the electronic structure of the cyclopro-pylcarbinyl cation, see: G. A. Olah, G. K. Surya Prakash, G. Rasul, J. Am. Chem. Soc. 2008, 130, 9168-9172.
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 9168-9172
    • Olah, G.A.1    Surya Prakash, G.K.2    Rasul, G.3
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    • See reference 19, 345f
    • See reference 19, 345f.
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    • • is only ∼2 kcal/mol: J. M. Nicovich, K. D. Kreutter, P. H. Wine, J. Chem. Phys. 1990, 92, 3539-3544.
    • • is only ∼2 kcal/mol: J. M. Nicovich, K. D. Kreutter, P. H. Wine, J. Chem. Phys. 1990, 92, 3539-3544.
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    • For this usage, see M. S. Platz, In Advances in Carbene Chemistry 2 (Ed.: U. H. Brinker) JAI Press: Stamford, CT 1998, 165f-168f.
    • For this usage, see M. S. Platz, In Advances in Carbene Chemistry Vol. 2 (Ed.: U. H. Brinker) JAI Press: Stamford, CT 1998, 165f-168f.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.