메뉴 건너뛰기




Volumn , Issue 14, 2007, Pages 2219-2232

Spin-center shift (SCS) - A versatile concept in biological and synthetic chemistry

Author keywords

Cyclization; DNA; Enzymes; Photochemistry; Radical reactions

Indexed keywords


EID: 34250629533     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600915     Document Type: Short Survey
Times cited : (82)

References (133)
  • 2
    • 34250629334 scopus 로고    scopus 로고
    • M. Regitz, B. Giese (Eds.), C-Radikale in Houben-Weyl Methods of Organic Chemistry, Georg Thieme, Stuttgart, 1989, E.19;
    • b) M. Regitz, B. Giese (Eds.), "C-Radikale" in Houben-Weyl Methods of Organic Chemistry, Georg Thieme, Stuttgart, 1989, vol. E.19;
  • 3
    • 0004269715 scopus 로고    scopus 로고
    • P. Renaud, M. P. Sibi Eds, Wiley-VCH, Weinheim, vols, and 2
    • c) P. Renaud, M. P. Sibi (Eds.), Radicals in Organic Synthesis, Wiley-VCH, Weinheim, 2001, vols. 1 and 2.
    • (2001) Radicals in Organic Synthesis , vol.1
  • 5
    • 0000489779 scopus 로고
    • a) P. A. Frey, Chem. Rev. 1990, 90, 1343-1357;
    • (1990) Chem. Rev , vol.90 , pp. 1343-1357
    • Frey, P.A.1
  • 12
    • 0000289664 scopus 로고    scopus 로고
    • Mechanistic Investigations of Ribonucleotide Reductases
    • Ed, C. D. Poulter, Elsevier, New York
    • b) S. Licht, J. Stubbe, "Mechanistic Investigations of Ribonucleotide Reductases" in Comprehensive Natural Products Chemistry (Ed.: C. D. Poulter), Elsevier, New York, 1999, vol. 5, p. 163-203.
    • (1999) Comprehensive Natural Products Chemistry , vol.5 , pp. 163-203
    • Licht, S.1    Stubbe, J.2
  • 28
    • 34250629742 scopus 로고    scopus 로고
    • The secondary C3′-O bond breaks 60 times faster than the C5′-O bond. For details, see ref.[11b].
    • The secondary C3′-O bond breaks 60 times faster than the C5′-O bond. For details, see ref.[11b].
  • 35
    • 34250626524 scopus 로고    scopus 로고
    • We have estimated the pKa value of the 2-hydroxy-2-propyl radical to be between 7 and 8. Therefore, the acidity of this radical intermediate is significantly higher than that of the corresponding alcohol (2-propanol, pKa, 16.5, Our estimation is based on high-level ab initio calculations using the complete basis set method CBS-QB3: a) O. Muehling, Ph. D. Dissertation, Humboldt-Universität zu Berlin, 2006, chapter 3, p. 49-50;
    • a = 16.5). Our estimation is based on high-level ab initio calculations using the complete basis set method CBS-QB3: a) O. Muehling, Ph. D. Dissertation, Humboldt-Universität zu Berlin, 2006, chapter 3, p. 49-50;
  • 50
    • 33845184544 scopus 로고
    • and references cited therein
    • L. J. Johnston, J. C. Scaiano, Chem. Rev. 1989, 89, 521-547, and references cited therein.
    • (1989) Chem. Rev , vol.89 , pp. 521-547
    • Johnston, L.J.1    Scaiano, J.C.2
  • 55
    • 27444444378 scopus 로고    scopus 로고
    • A. G. Griesbeck, S. Bondock, Oxetane Formation: Stereocontrol in Organic Photochemistry and Photobiology, 2nd ed. (Eds.: W. M. Horspool, F. Lenci), CRC Press, Boca Raton, FL, 2003, p. 59/1-59/19;
    • b) A. G. Griesbeck, S. Bondock, "Oxetane Formation: Stereocontrol" in Organic Photochemistry and Photobiology, 2nd ed. (Eds.: W. M. Horspool, F. Lenci), CRC Press, Boca Raton, FL, 2003, p. 59/1-59/19;
  • 56
    • 85056343377 scopus 로고    scopus 로고
    • A. G. Griesbeck, S. Bondock, Oxetane Formation: Intermolecular Additions in Organic Photochemistry and Photobiology, 2nd ed. (Eds.: W. M. Horspool, F. Lenci), CRC Press, Boca Raton, FL, 2003, p. 60/1-60/21;
    • c) A. G. Griesbeck, S. Bondock, "Oxetane Formation: Intermolecular Additions" in Organic Photochemistry and Photobiology, 2nd ed. (Eds.: W. M. Horspool, F. Lenci), CRC Press, Boca Raton, FL, 2003, p. 60/1-60/21;
  • 57
    • 84959317863 scopus 로고    scopus 로고
    • for other photocycloaddition reactions, see: d >B. Grosch, T. Bach, Enantioselective Photocycloaddition Reactions in Solution in Organic Photochemistry and Photobiology, 2nd ed. (Eds.: W. M. Horspool, F. Lenci), CRC Press, Boca Raton, FL, 2003, p. 61/1-61/14;
    • for other photocycloaddition reactions, see: d) >B. Grosch, T. Bach, "Enantioselective Photocycloaddition Reactions in Solution" in Organic Photochemistry and Photobiology, 2nd ed. (Eds.: W. M. Horspool, F. Lenci), CRC Press, Boca Raton, FL, 2003, p. 61/1-61/14;
  • 58
    • 85056330624 scopus 로고    scopus 로고
    • M. Abe, Photochemical Oxetane Formation: Addition to Heterocycles in Organic Photochemistry and Photobiology, 2nd ed. (Eds.: W. M. Horspool, F. Lenci), CRC Press, Boca Raton, FL, 2003, p. 62/1-62/10;
    • e) M. Abe, "Photochemical Oxetane Formation: Addition to Heterocycles" in Organic Photochemistry and Photobiology, 2nd ed. (Eds.: W. M. Horspool, F. Lenci), CRC Press, Boca Raton, FL, 2003, p. 62/1-62/10;
  • 59
    • 0031955099 scopus 로고    scopus 로고
    • for other [2+2] photocycloaddition reactions, see: f T. Bach, Synthesis 1998, 683-703.
    • for other [2+2] photocycloaddition reactions, see: f) T. Bach, Synthesis 1998, 683-703.
  • 60
    • 33947292229 scopus 로고
    • For a selection of reviews, see: a
    • For a selection of reviews, see: a) P. J. Wagner, Acc. Chem. Res. 1971, 4, 168-177;
    • (1971) Acc. Chem. Res , vol.4 , pp. 168-177
    • Wagner, P.J.1
  • 63
    • 85052764806 scopus 로고
    • Photoinduced Hydrogen Atom Abstraction by Carbonyl Compounds
    • Ed, A. Padwa, Marcel Dekker, New York
    • d) P. J. Wagner, B. S. Park, "Photoinduced Hydrogen Atom Abstraction by Carbonyl Compounds" in Organic Photochemistry (Ed.: A. Padwa), Marcel Dekker, New York, 1991, vol. 11, p. 227-366;
    • (1991) Organic Photochemistry , vol.11 , pp. 227-366
    • Wagner, P.J.1    Park, B.S.2
  • 64
    • 84964805623 scopus 로고    scopus 로고
    • P. J. Wagner, P. Klán, Norrish Type II Photoelimination of Ketones: Cleavage of 1,4-Biradicals Formed by γ-Hydrogen Abstraction in Organic Photochemistry and Photobiology, 2nd ed. (Eds.: W. M. Horspool, F. Lenci), CRC Press, Boca Raton, FL, 2003, p. 52/1-52/31;
    • e) P. J. Wagner, P. Klán, "Norrish Type II Photoelimination of Ketones: Cleavage of 1,4-Biradicals Formed by γ-Hydrogen Abstraction" in Organic Photochemistry and Photobiology, 2nd ed. (Eds.: W. M. Horspool, F. Lenci), CRC Press, Boca Raton, FL, 2003, p. 52/1-52/31;
  • 65
    • 85056356739 scopus 로고    scopus 로고
    • T. Hasegawa, Norrish Type II Processes of Ketones: Influence of Environment in Organic Photochemistry and Photobiology, 2nd ed. (Eds.: W. M. Horspool, F. Lenci), CRC Press, Boca Raton, FL, 2003, p. 55/1-55/14;
    • f) T. Hasegawa, "Norrish Type II Processes of Ketones: Influence of Environment" in Organic Photochemistry and Photobiology, 2nd ed. (Eds.: W. M. Horspool, F. Lenci), CRC Press, Boca Raton, FL, 2003, p. 55/1-55/14;
  • 66
    • 27444432380 scopus 로고    scopus 로고
    • P. Wessig, Regioselective Photochemical Synthesis of Carbo- and Heterocyclic Compounds: The Norrish Yang Reaction in Organic Photochemistry and Photobiology, 2nd ed. (Eds.: W. M. Horspool, F. Lenci), CRC Press, Boca Raton, FL, 2003, p. 57/1-57/20;
    • g) P. Wessig, "Regioselective Photochemical Synthesis of Carbo- and Heterocyclic Compounds: The Norrish Yang Reaction" in Organic Photochemistry and Photobiology, 2nd ed. (Eds.: W. M. Horspool, F. Lenci), CRC Press, Boca Raton, FL, 2003, p. 57/1-57/20;
  • 67
    • 85056329043 scopus 로고    scopus 로고
    • P. J. Wagner, Yang Photocyclization: Coupling of Biradicals Formed by Intramolecular Hydrogen Abstraction in Organic Photochemistry and Photobiology, 2nd ed. (Eds.: W. M. Horspool, F. Lenci), CRC Press, Boca Raton, FL, 2003, p. 58/1-58/70;
    • h) P. J. Wagner, "Yang Photocyclization: Coupling of Biradicals Formed by Intramolecular Hydrogen Abstraction" in Organic Photochemistry and Photobiology, 2nd ed. (Eds.: W. M. Horspool, F. Lenci), CRC Press, Boca Raton, FL, 2003, p. 58/1-58/70;
  • 68
    • 34247244934 scopus 로고    scopus 로고
    • Abstraction of γ-Hydrogens by Excited Carbonyls
    • Eds, A. G. Griesbeck, J. Mattay, Marcel Dekker, New York
    • i) P. J. Wagner, "Abstraction of γ-Hydrogens by Excited Carbonyls" in Molecular and Supramolecular Photochemistry (Eds.: A. G. Griesbeck, J. Mattay), Marcel Dekker, New York, 2005, vol. 12, p. 11-39.
    • (2005) Molecular and Supramolecular Photochemistry , vol.12 , pp. 11-39
    • Wagner, P.J.1
  • 71
    • 27444436761 scopus 로고    scopus 로고
    • Abstraction of (γ±n) -Hydrogens by Excited Carbonyls
    • Eds, A. G. Griesbeck, J. Mattay, Marcel Dekker, New York
    • a) P. Wessig, O. Muehling, "Abstraction of (γ±n) -Hydrogens by Excited Carbonyls" in Molecular and Supramolecular Photochemistry (Eds.: A. G. Griesbeck, J. Mattay), Marcel Dekker, New York, 2005, vol. 12, p. 41-87;
    • (2005) Molecular and Supramolecular Photochemistry , vol.12 , pp. 41-87
    • Wessig, P.1    Muehling, O.2
  • 72
    • 34250655822 scopus 로고    scopus 로고
    • Stereoselective Photocyclization of Ketones (Norrish-Yang Reaction)
    • Ed, G. Dyker, Wiley-VCH, Weinheim
    • b) P. Wessig, "Stereoselective Photocyclization of Ketones (Norrish-Yang Reaction)" in Handbook of C-H Transformations (Ed.: G. Dyker), Wiley-VCH, Weinheim, 2005, vol. 2, p. 569-579.
    • (2005) Handbook of C-H Transformations , vol.2 , pp. 569-579
    • Wessig, P.1
  • 74
    • 0035857554 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2001, 40, 1064-1065;
    • (2001) Chem. Int. Ed , vol.40 , pp. 1064-1065
    • Angew1
  • 77
    • 27444442782 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 6778-6781;
    • (2005) Chem. Int. Ed , vol.44 , pp. 6778-6781
    • Angew1
  • 83
    • 85056341436 scopus 로고    scopus 로고
    • J. R. Scheffer, C. Scott, Crystal Structure-Solid State Reactivity Relationships: Toward a Greater Understanding of Norrish/Yang Type II Photochemistry in Organic Photochemistry and Photobiology, 2nd ed. (Eds.: W. M. Horspool, F. Lenci), CRC Press, Boca Raton, FL, 2003, p. 54/1-54/25;
    • b) J. R. Scheffer, C. Scott, "Crystal Structure-Solid State Reactivity Relationships: Toward a Greater Understanding of Norrish/Yang Type II Photochemistry" in Organic Photochemistry and Photobiology, 2nd ed. (Eds.: W. M. Horspool, F. Lenci), CRC Press, Boca Raton, FL, 2003, p. 54/1-54/25;
  • 98
    • 34250639954 scopus 로고    scopus 로고
    • A previous report on the formation of cyclopropanols (H.-G. Henning, R. Berlinghoff, A. Mahlow, H. Köppel, K. D. Schleinitz, J. Prakt. Chem. 1981, 323, 914-918)
    • A previous report on the formation of cyclopropanols (H.-G. Henning, R. Berlinghoff, A. Mahlow, H. Köppel, K. D. Schleinitz, J. Prakt. Chem. 1981, 323, 914-918)
  • 99
    • 0001649913 scopus 로고    scopus 로고
    • seems to be based on a mistake in the interpretation of the spectroscopic data: U. Lindemann, M. Neuburger, M. Neuburger-Zehnder, D. Wulff-Molder, P. Wessig, J. Chem. Soc., Perkin Trans. 2 1999, 2029-2036.
    • seems to be based on a mistake in the interpretation of the spectroscopic data: U. Lindemann, M. Neuburger, M. Neuburger-Zehnder, D. Wulff-Molder, P. Wessig, J. Chem. Soc., Perkin Trans. 2 1999, 2029-2036.
  • 102
    • 0000782249 scopus 로고    scopus 로고
    • Kinetics of Radical Reactions: Radical Clocks
    • Eds, P. Renaud, M. P. Sibi, Wiley-VCH, Weinheim, and references cited therein
    • M. Newcomb, "Kinetics of Radical Reactions: Radical Clocks" in Radicals in Organic Synthesis (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim, 2001, vol. 1, p. 317-336, and references cited therein.
    • (2001) Radicals in Organic Synthesis , vol.1 , pp. 317-336
    • Newcomb, M.1
  • 104
    • 0033972186 scopus 로고    scopus 로고
    • 0 [ln(A/B) = 0]: a) Y. Inoue, H. Ikeda, M. Kaneda, T. Sumimura, S. R. L. Everitt, T. Wada, J. Am. Chem. Soc. 2000, 122, 406-407, and references cited therein;
    • 0 [ln(A/B) = 0]: a) Y. Inoue, H. Ikeda, M. Kaneda, T. Sumimura, S. R. L. Everitt, T. Wada, J. Am. Chem. Soc. 2000, 122, 406-407, and references cited therein;
  • 107
    • 0037051959 scopus 로고    scopus 로고
    • W. Adam, V. R. Stegmann, J. Am. Chem. Soc. 2002, 124, 3600-3607, and references cited therein;
    • d) W. Adam, V. R. Stegmann, J. Am. Chem. Soc. 2002, 124, 3600-3607, and references cited therein;
  • 111
    • 0001101060 scopus 로고
    • For publications dealing with the influence of reaction parameters temperature, solvent, etc, on the selectivity as well as with the compensation of entropic and enthalpic factors, see, for the isoinversion principle: a
    • For publications dealing with the influence of reaction parameters (temperature, solvent, etc.) on the selectivity as well as with the compensation of entropic and enthalpic factors, see, for the isoinversion principle: a) H. Buschmann, H.-D. Scharf, N. Hoffmann, P. Esser, Angew. Chem. 1991, 103, 480-518;
    • (1991) Angew. Chem , vol.103 , pp. 480-518
    • Buschmann, H.1    Scharf, H.-D.2    Hoffmann, N.3    Esser, P.4
  • 112
    • 0025780257 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. Engl. 1991, 30, 477-515 and references cited therein;
    • Angew. Chem. Int. Ed. Engl. 1991, 30, 477-515 and references cited therein;
  • 113
    • 0001459567 scopus 로고
    • for isoselectivity relationships, see: b
    • for isoselectivity relationships, see: b) B. Giese, Acc. Chem. Res. 1984, 17, 438-442;
    • (1984) Acc. Chem. Res , vol.17 , pp. 438-442
    • Giese, B.1
  • 117
    • 0003038928 scopus 로고    scopus 로고
    • For reviews, see: a
    • For reviews, see: a) G. F. Koser, Aldrichimica Acta 2001, 34, 89-102;
    • (2001) Aldrichimica Acta , vol.34 , pp. 89-102
    • Koser, G.F.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.