메뉴 건너뛰기




Volumn 69, Issue 16, 2004, Pages 5281-5289

Photolysis of 1-alkylcycloalkanols in the presence of (diacetoxyiodo) benzene and I2. Intramolecular selectivity in the β-scission reactions of the intermediate 1-alkylcycloalkoxyl radicals

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; BENZENE; CHEMICAL BONDS; HYDROGEN; PHOTOLYSIS; SOLUTIONS; SUBSTITUTION REACTIONS;

EID: 3543007143     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049524y     Document Type: Article
Times cited : (31)

References (56)
  • 2
    • 0031077875 scopus 로고    scopus 로고
    • See, for example: Orlando, J. J.; Tyndall, G. S.; Wallington, T. J. Chem. Rev. 2003, 103, 4657-4689. Atkinson, R. Int. J. Chem. Kinet. 1997, 29, 99-111.
    • (1997) Int. J. Chem. Kinet. , vol.29 , pp. 99-111
    • Atkinson, R.1
  • 3
    • 0036591861 scopus 로고    scopus 로고
    • See, for example: Davies, M. J.; Headlam, H. A. Free Rad. Biol. Med. 2002, 32, 1171-1184. Halliwell, B.; Gutteridge, J. M. C. Free Radicals in Biology and Medicine, 3rd ed.; Oxford University Press: New York, 1999. Cumming, J. N.; Ploypradith, P.; Posner, G. H. Adv. Pharmacol. 1997, 37, 2253-2297. Ullrich, V.; Brugger, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1911-1919.
    • (2002) Free Rad. Biol. Med. , vol.32 , pp. 1171-1184
    • Davies, M.J.1    Headlam, H.A.2
  • 4
    • 0036591861 scopus 로고    scopus 로고
    • Oxford University Press: New York
    • See, for example: Davies, M. J.; Headlam, H. A. Free Rad. Biol. Med. 2002, 32, 1171-1184. Halliwell, B.; Gutteridge, J. M. C. Free Radicals in Biology and Medicine, 3rd ed.; Oxford University Press: New York, 1999. Cumming, J. N.; Ploypradith, P.; Posner, G. H. Adv. Pharmacol. 1997, 37, 2253-2297. Ullrich, V.; Brugger, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1911-1919.
    • (1999) Free Radicals in Biology and Medicine, 3rd Ed.
    • Halliwell, B.1    Gutteridge, J.M.C.2
  • 5
    • 0036591861 scopus 로고    scopus 로고
    • See, for example: Davies, M. J.; Headlam, H. A. Free Rad. Biol. Med. 2002, 32, 1171-1184. Halliwell, B.; Gutteridge, J. M. C. Free Radicals in Biology and Medicine, 3rd ed.; Oxford University Press: New York, 1999. Cumming, J. N.; Ploypradith, P.; Posner, G. H. Adv. Pharmacol. 1997, 37, 2253-2297. Ullrich, V.; Brugger, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1911-1919.
    • (1997) Adv. Pharmacol. , vol.37 , pp. 2253-2297
    • Cumming, J.N.1    Ploypradith, P.2    Posner, G.H.3
  • 6
    • 0027995192 scopus 로고
    • See, for example: Davies, M. J.; Headlam, H. A. Free Rad. Biol. Med. 2002, 32, 1171-1184. Halliwell, B.; Gutteridge, J. M. C. Free Radicals in Biology and Medicine, 3rd ed.; Oxford University Press: New York, 1999. Cumming, J. N.; Ploypradith, P.; Posner, G. H. Adv. Pharmacol. 1997, 37, 2253-2297. Ullrich, V.; Brugger, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1911-1919.
    • (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 1911-1919
    • Ullrich, V.1    Brugger, R.2
  • 8
    • 0035131973 scopus 로고    scopus 로고
    • Hartung, J.; Kneuer, R.; Laug, S.; Schmidt, P.; Špehar, K.; Svoboda, I.; Fuess, H. Eur. J. Org. Chem. 2003, 4033-4052. Hartung, J. Eur. J. Org. Chem. 2001, 619-632. Hartung, J. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, pp 427-439.
    • (2001) Eur. J. Org. Chem. , pp. 619-632
    • Hartung, J.1
  • 9
    • 0242386424 scopus 로고    scopus 로고
    • Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim
    • Hartung, J.; Kneuer, R.; Laug, S.; Schmidt, P.; Špehar, K.; Svoboda, I.; Fuess, H. Eur. J. Org. Chem. 2003, 4033-4052. Hartung, J. Eur. J. Org. Chem. 2001, 619-632. Hartung, J. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, pp 427-439.
    • (2001) Radicals in Organic Synthesis , vol.2 , pp. 427-439
    • Hartung, J.1
  • 10
    • 0000213430 scopus 로고    scopus 로고
    • Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim
    • (a) Suárez, E.; Rodriguez, M. S. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, pp 440-454.
    • (2001) Radicals in Organic Synthesis , vol.2 , pp. 440-454
    • Suárez, E.1    Rodriguez, M.S.2
  • 11
    • 0000124573 scopus 로고    scopus 로고
    • Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim
    • (b) Zhang, W. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, pp 234-245.
    • (2001) Radicals in Organic Synthesis , vol.2 , pp. 234-245
    • Zhang, W.1
  • 12
    • 0033618523 scopus 로고    scopus 로고
    • (c) Yet, L. Tetrahedron 1999, 55, 9349-9403.
    • (1999) Tetrahedron , vol.55 , pp. 9349-9403
    • Yet, L.1
  • 15
  • 37
    • 3542991206 scopus 로고    scopus 로고
    • note
    • The possibility that iodoalkane formation occurs through an iodine transfer step from the hypoiodite, precursor of the alkoxyl radical, should also be considered. We thank a reviewer for drawing our attention on this point.
  • 43
    • 3543034375 scopus 로고    scopus 로고
    • note
    • -1, respectively (see ref 27).
  • 47
    • 3543039742 scopus 로고    scopus 로고
    • note
    • In a first approximation, by assuming similar rate constants for C-R bond cleavage in the 1-propylcyclohexoxyl and 1-propylcycloheptoxyl radicals, comparison between the Q ratios obtained from the reactions of the two radicals (Q = 0.06 for the 1-propylcyclohexoxyl radical and Q = 0.75 for the 1-propylcycloheptoxyl one) suggests that ring-opening of the former radical is faster than that of the latter one, a finding which, however, is in contrast with the significantly greater ring strain associated to a seven-membered ring as compared to a six-membered one. Moreover, such an assumption does not take into account that the differences in strain between the radical and the product cycloalkanone should be significantly different in the two systems (see ref 16), and accordingly different rates of C-R cleavage can be reasonably expected for the two radicals.
  • 50
    • 3543033773 scopus 로고    scopus 로고
    • note
    • For example an increase between 10 and 20 times (depending on solvent) in the rate constant for C-Me β-scission is observed on going from the tert-butoxyl radical (see ref 36) to the cumyloxyl one (see refs 19 and 37).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.