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Volumn 111, Issue 5, 2011, Pages 3268-3333

Ring expansion of cyclobutylmethylcarbenium ions to cyclopentane or cyclopentene derivatives and metal-promoted analogous rearrangements

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL GROUPS; CARBOCYCLIC RINGS; CYCLIZATION REACTIONS; CYCLOBUTANE RING; CYCLOPENTENES; LEAVING GROUPS; PROPYLENE OXIDE; RING EXPANSION; SPIROCYCLIZATION;

EID: 79955925389     PISSN: 00092665     EISSN: 15206890     Source Type: Journal    
DOI: 10.1021/cr100295j     Document Type: Review
Times cited : (130)

References (475)
  • 10
    • 79955889162 scopus 로고
    • De Mayo P. In;, Ed.; Wiley Interscience: New York,; pp .
    • Breslow, R. In Molecular Rearrangements; de Mayo, P., Ed.; Wiley Interscience: New York, 1963; pp 276 - 280.
    • (1963) Molecular Rearrangements , pp. 276-280
    • Breslow, R.1
  • 11
    • 0005700510 scopus 로고
    • The strain energies (kcal/mol) of cyclopropane (28.13), cyclobutane (26.90), cyclopentane (7.19), and cyclohexane (1.35), estimated based on single conformation increments
    • The strain energies (kcal/mol) of cyclopropane (28.13), cyclobutane (26.90), cyclopentane (7.19), and cyclohexane (1.35), estimated based on single conformation increments; Schleyer, P. v. R.; Williams, J. E.; Blanchard, K. R. J. Am. Chem. Soc. 1970, 92, 2377
    • (1970) J. Am. Chem. Soc. , vol.92 , pp. 2377
    • Schleyer V. P, R.1    Williams, J.E.2    Blanchard, K.R.3
  • 19
    • 0001380978 scopus 로고
    • Vol.; Wiley: New York,; p.
    • Smith, P. A.; Baer, D. R. Org. React., Vol. 11; Wiley: New York, 1960; p 157.
    • (1960) Org. React. , vol.11 , pp. 157
    • Smith, P.A.1    Baer, D.R.2
  • 20
    • 0000688199 scopus 로고
    • Trost B.M. Fleming I. Pattenden G. Rickborn B..I. Coveney D.J. For an overview of Wagner-Meerwein rearrangements and related reactions, see: In;;;, Eds.; Pergamon Press: Oxford, U.K.,; Vol., Chapter 3.1, Chapter 3.2, pp 721 - 732, and Chapter 3.3, pp 733 - 776.; Chapter 3.4, pp 777 - 802.
    • For an overview of Wagner-Meerwein rearrangements and related reactions, see: Hanson, J. R. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Pattenden, G., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 3, Chapter 3.1, pp 705 - 720. Rickborn, B., idem; Chapter 3.2, pp 721 - 732, and Chapter 3.3, pp 733 - 776. Coveney, D. J.; Chapter 3.4, pp 777 - 802.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 705-720
    • Hanson, J.R.1
  • 27
    • 0001295110 scopus 로고
    • New Synthetic Pathways from Cyclobutanones
    • Halton B. In, Vol.;, Ed.; JAI Press: Greenwich, CN.
    • Lee-Ruff, E. New Synthetic Pathways from Cyclobutanones. In Advanced Strain in Organic Chemistry, Vol. 1; Halton, B., Ed.; JAI Press: Greenwich, CN, 1991.
    • (1991) Advanced Strain in Organic Chemistry , vol.1
    • Lee-Ruff, E.1
  • 36
    • 84948503533 scopus 로고
    • For a review on jasmonoid synthesis, see
    • For a review on jasmonoid synthesis, see: Ho, T.-L. Synth. Commun. 1974, 4, 265
    • (1974) Synth. Commun. , vol.4 , pp. 265
    • Ho, T.-L.1
  • 43
    • 0342545127 scopus 로고    scopus 로고
    • De Meijere A. Ed.; Georg Thieme Verlag: Stuttgart, Germany,; Vol., pp .
    • Wong, H. C. N. Houben-Weyl Methods of Organic Chemistry; de Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, Germany, 1997; Vol. E17e, pp 495 - 515.
    • (1997) Houben-Weyl Methods of Organic Chemistry , vol.17 , pp. 495-515
    • Wong, H.C.N.1
  • 59
    • 79955900038 scopus 로고
    • 2 nd ed.; Cambridge University Press: London,; Vol., pp, 171.
    • Simonsen, J. L. The Terpenes, 2 nd ed.; Cambridge University Press: London, 1949; Vol. II, pp 156, 171.
    • (1949) The Terpenes , vol.2 , pp. 156
    • Simonsen, J.L.1
  • 72
    • 79955879351 scopus 로고    scopus 로고
    • Chem. Abstr. 2001, 136, 386264.
    • (2001) Chem. Abstr. , vol.136 , pp. 386264
  • 88
    • 84916492738 scopus 로고
    • Nozaki N. Ed.;, Ed.; Pergamon Press: Oxford and New York,; p.
    • Mikolajczyk, M. Current Trends in Organic Synthesis, Ed.; Nozaki, N., Ed.; Pergamon Press: Oxford and New York, 1983; p 347.
    • (1983) Current Trends in Organic Synthesis , pp. 347
    • Mikolajczyk, M.1
  • 157
    • 84942755909 scopus 로고
    • Wilkinson G. Stone F.G.A. Abel E.W. In;;;, Eds.; Pergamon Press: New York,; Vol., pp .
    • McKillop, A.; Taylor, E. C. In Comprehensive Organometallic Chemistry; Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 7, pp 465 - 513.
    • (1982) Comprehensive Organometallic Chemistry , vol.7 , pp. 465-513
    • McKillop, A.1    Taylor, E.C.2
  • 166
    • 0000903824 scopus 로고
    • For studies on the intermolecular carbopalladation of allenes, see
    • For studies on the intermolecular carbopalladation of allenes, see: Yamamoto, Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 6019
    • Yamamoto, Y.1    Al-Masum, M.2    Asao, N.3
  • 171
    • 0028064401 scopus 로고
    • For studies on the intramolecular carbopalladation of allenes, see
    • For studies on the intramolecular carbopalladation of allenes, see: Ma, S.; Negishi, E. J. Org. Chem. 1994, 59, 4730
    • (1994) J. Org. Chem. , vol.59 , pp. 4730
    • Ma, S.1    Negishi, E.2
  • 189
    • 0000931564 scopus 로고
    • For reviews on palladium-catalyzed reactions of propargylic compounds, see
    • For reviews on palladium-catalyzed reactions of propargylic compounds, see: Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140
    • (1987) Acc. Chem. Res. , vol.20 , pp. 140
    • Tsuji, J.1    Minami, I.2
  • 229
    • 33845471716 scopus 로고
    • Compare the heats of formation (kcal/mol) of the primary (201), secondary (183), and tertiary butylcarbenium ion (166):;, and references therein
    • Compare the heats of formation (kcal/mol) of the primary (201), secondary (183), and tertiary butylcarbenium ion (166): Lossing, F. P.; Holmes, J. L. J. Am. Chem. Soc. 1984, 106, 6917 and references therein
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 6917
    • Lossing, F.P.1    Holmes, J.L.2
  • 301
    • 0000356602 scopus 로고
    • For reviews on the diazomethane ring expansion reaction, see
    • For reviews on the diazomethane ring expansion reaction, see: Gutsche, C. D. Org. React. 1954, 8, 364
    • (1954) Org. React. , vol.8 , pp. 364
    • Gutsche, C.D.1
  • 370
    • 0004104868 scopus 로고
    • De Mayo P. If alternative 1,2-shifts can occur, the bond which forms the smaller dihedral angle with the vacant p-orbital, will be broken:;; In;, Ed.; Academic Press: New York,; Vol.
    • If alternative 1,2-shifts can occur, the bond which forms the smaller dihedral angle with the vacant p-orbital, will be broken: Saunders, M.; Chandrasekhar, J.; Schleyer, P. v. R. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 1.
    • (1980) Rearrangements in Ground and Excited States , vol.1
    • Saunders, M.1    Chandrasekhar, J.2    Schleyer V. P, R.3
  • 371
    • 79955905868 scopus 로고    scopus 로고
    • f° = -18.5 kcal/mol).
    • f° = -18.5 kcal/mol).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.