메뉴 건너뛰기




Volumn 7, Issue 9, 2001, Pages 2028-2033

Phosphinofenchol or metastable phosphorane? Phosphorus derivatives of fenchol

Author keywords

Chirality; Density functional calculations; P ligands; Phosphorus; Thermochemistry

Indexed keywords

ALKYLATION; BENZENE; ISOMERS; SYNTHESIS (CHEMICAL); THERMODYNAMIC STABILITY; X RAY ANALYSIS;

EID: 85047699820     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (22)

References (61)
  • 3
    • 0012397313 scopus 로고
    • Directed metallation groups (DMGs): V. Snieckus, Chem. Rev. 1990, 90, 879-933.
    • (1990) Chem. Rev. , vol.90 , pp. 879-933
    • Snieckus, V.1
  • 15
    • 0034680550 scopus 로고    scopus 로고
    • b) B. Goldfuss, M. Steigelmann, F. Rominger. Angew. Chem. 2000, 112, 4299-4302; Angew. Chem. Int. Ed. 2000, 39, 4133-4136.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 4133-4136
  • 17
    • 0031054486 scopus 로고    scopus 로고
    • For phosphine ligands based on the camphor skeleton see: a) I. V. Komarov, M. V. Gorichko, M. Y. Kornilov, Tetrahedron: Asymmetry 1997, 8, 435-445; Brunner's NORPHOS is a highly prominent bicyclo[2.2.1]heptane derivative: b) H. Brunner, W. Pieronczyk, Angew. Chem. 1979, 91, 655-656; Angew. Chem. Int. Ed. Engl. 1979, 18, 620.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 435-445
    • Komarov, I.V.1    Gorichko, M.V.2    Kornilov, M.Y.3
  • 18
    • 0031054486 scopus 로고    scopus 로고
    • For phosphine ligands based on the camphor skeleton see: a) I. V. Komarov, M. V. Gorichko, M. Y. Kornilov, Tetrahedron: Asymmetry 1997, 8, 435-445; Brunner's NORPHOS is a highly prominent bicyclo[2.2.1]heptane derivative: b) H. Brunner, W. Pieronczyk, Angew. Chem. 1979, 91, 655-656; Angew. Chem. Int. Ed. Engl. 1979, 18, 620.
    • (1979) Angew. Chem. , vol.91 , pp. 655-656
    • Brunner, H.1    Pieronczyk, W.2
  • 19
    • 84985598655 scopus 로고
    • For phosphine ligands based on the camphor skeleton see: a) I. V. Komarov, M. V. Gorichko, M. Y. Kornilov, Tetrahedron: Asymmetry 1997, 8, 435-445; Brunner's NORPHOS is a highly prominent bicyclo[2.2.1]heptane derivative: b) H. Brunner, W. Pieronczyk, Angew. Chem. 1979, 91, 655-656; Angew. Chem. Int. Ed. Engl. 1979, 18, 620.
    • (1979) Angew. Chem. Int. Ed. Engl. , vol.18 , pp. 620
  • 20
    • 2742542064 scopus 로고
    • For applications of 2-(diphenylphosphino)benzoic acid in ligand systems see: a) B. M. Trost, B. Breit, S. Peukert, J. Zambrano, J. W. Ziller, Angew. Chem. 1995, 107, 2577-2579; Angew. Chem. Int. Ed. Engl. 1995, 34, 2386-2388;
    • (1995) Angew. Chem. , vol.107 , pp. 2577-2579
    • Trost, B.M.1    Breit, B.2    Peukert, S.3    Zambrano, J.4    Ziller, J.W.5
  • 21
    • 33748741518 scopus 로고
    • For applications of 2-(diphenylphosphino)benzoic acid in ligand systems see: a) B. M. Trost, B. Breit, S. Peukert, J. Zambrano, J. W. Ziller, Angew. Chem. 1995, 107, 2577-2579; Angew. Chem. Int. Ed. Engl. 1995, 34, 2386-2388;
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 2386-2388
  • 34
    • 0002941903 scopus 로고
    • For biphenyl based spiro-phosphoranes see: a) D. Hellwinkel, Top. Curr. Chem. 1983, 109, 1-63;
    • (1983) Top. Curr. Chem. , vol.109 , pp. 1-63
    • Hellwinkel, D.1
  • 40
    • 0000189651 scopus 로고
    • The B3LYP-hybrid-DFT method: a) Becke, J. Chem. Phys. 1993, 98, 5648-5652; b) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
    • (1993) J. Chem. Phys. , vol.98 , pp. 5648-5652
    • Becke1
  • 41
    • 0345491105 scopus 로고
    • The B3LYP-hybrid-DFT method: a) Becke, J. Chem. Phys. 1993, 98, 5648-5652; b) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
    • (1988) Phys. Rev. B , vol.37 , pp. 785-789
    • Lee, C.1    Yang, W.2    Parr, R.G.3
  • 44
    • 85007631010 scopus 로고    scopus 로고
    • The gas phase computations do not consider polar solvent effects or hydrogen bonds, which should even more stabilize hydroxy groups
    • The gas phase computations do not consider polar solvent effects or hydrogen bonds, which should even more stabilize hydroxy groups.
  • 45
    • 0011805675 scopus 로고
    • 5 see: a) W. Kutzelnigg, J. Wasilewski, J. Am. Chem. Soc. 1982, 104, 953-960: for examples of unusually coordinated phosphorus compounds see: b) F. Zurmuehlen, M. Regitz, New J. Chem. 1989, 13, 335-340; c) F. Zurmuehlen, M. Regitz, Angew. Chem. 1987, 99, 65-67: Angew. Chem. Int. Ed. Engl. 1987, 26, 83-85; c) F. Zurmuehlen, W. Roesch, M. Regitz, Z. Naturforsch. 1985, 40B, 1077-1086.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 953-960
    • Kutzelnigg, W.1    Wasilewski, J.2
  • 46
    • 0011805675 scopus 로고
    • 5 see: a) W. Kutzelnigg, J. Wasilewski, J. Am. Chem. Soc. 1982, 104, 953-960: for examples of unusually coordinated phosphorus compounds see: b) F. Zurmuehlen, M. Regitz, New J. Chem. 1989, 13, 335-340; c) F. Zurmuehlen, M. Regitz, Angew. Chem. 1987, 99, 65-67: Angew. Chem. Int. Ed. Engl. 1987, 26, 83-85; c) F. Zurmuehlen, W. Roesch, M. Regitz, Z. Naturforsch. 1985, 40B, 1077-1086.
    • (1989) New J. Chem. , vol.13 , pp. 335-340
    • Zurmuehlen, F.1    Regitz, M.2
  • 47
    • 0011805675 scopus 로고
    • 5 see: a) W. Kutzelnigg, J. Wasilewski, J. Am. Chem. Soc. 1982, 104, 953-960: for examples of unusually coordinated phosphorus compounds see: b) F. Zurmuehlen, M. Regitz, New J. Chem. 1989, 13, 335-340; c) F. Zurmuehlen, M. Regitz, Angew. Chem. 1987, 99, 65-67: Angew. Chem. Int. Ed. Engl. 1987, 26, 83-85; c) F. Zurmuehlen, W. Roesch, M. Regitz, Z. Naturforsch. 1985, 40B, 1077-1086.
    • (1987) Angew. Chem. , vol.99 , pp. 65-67
    • Zurmuehlen, F.1    Regitz, M.2
  • 48
    • 0011805675 scopus 로고
    • 5 see: a) W. Kutzelnigg, J. Wasilewski, J. Am. Chem. Soc. 1982, 104, 953-960: for examples of unusually coordinated phosphorus compounds see: b) F. Zurmuehlen, M. Regitz, New J. Chem. 1989, 13, 335-340; c) F. Zurmuehlen, M. Regitz, Angew. Chem. 1987, 99, 65-67: Angew. Chem. Int. Ed. Engl. 1987, 26, 83-85; c) F. Zurmuehlen, W. Roesch, M. Regitz, Z. Naturforsch. 1985, 40B, 1077-1086.
    • (1987) Angew. Chem. Int. Ed. Engl. , vol.26 , pp. 83-85
  • 49
    • 0011543368 scopus 로고
    • 5 see: a) W. Kutzelnigg, J. Wasilewski, J. Am. Chem. Soc. 1982, 104, 953-960: for examples of unusually coordinated phosphorus compounds see: b) F. Zurmuehlen, M. Regitz, New J. Chem. 1989, 13, 335-340; c) F. Zurmuehlen, M. Regitz, Angew. Chem. 1987, 99, 65-67: Angew. Chem. Int. Ed. Engl. 1987, 26, 83-85; c) F. Zurmuehlen, W. Roesch, M. Regitz, Z. Naturforsch. 1985, 40B, 1077-1086.
    • (1985) Z. Naturforsch. , vol.40 B , pp. 1077-1086
    • Zurmuehlen, F.1    Roesch, W.2    Regitz, M.3
  • 51
    • 85007650199 scopus 로고    scopus 로고
    • 31P NMR spectroscopy
    • 31P NMR spectroscopy.
  • 52
    • 85007633559 scopus 로고    scopus 로고
    • The smaller exo/endo differentiation probably originates from the smaller steric demand of the methylene group, relative to the bulkier alkyl moiety
    • The smaller exo/endo differentiation probably originates from the smaller steric demand of the methylene group, relative to the bulkier alkyl moiety.
  • 53
    • 85007628519 scopus 로고    scopus 로고
    • T. Löschmann, Diplomarbeit, Universität Heidelberg, 2000
    • T. Löschmann, Diplomarbeit, Universität Heidelberg, 2000.
  • 54
    • 85007627111 scopus 로고    scopus 로고
    • 31P NMR or IR), from which no X-ray crystal analysis could be obtained so far
    • 31P NMR or IR), from which no X-ray crystal analysis could be obtained so far.
  • 55
    • 85007627110 scopus 로고    scopus 로고
    • The apical P-Ph alignment of the X-ray crystal structure is not reproduced by the ONIOM optimization, due to the employment of hydrogen linker atoms at phosphorous
    • The apical P-Ph alignment of the X-ray crystal structure is not reproduced by the ONIOM optimization, due to the employment of hydrogen linker atoms at phosphorous.
  • 56
    • 0000594407 scopus 로고
    • For the formation of lithium phosphoranides from lithium alkoxides see ref. [12] and: J. Li, P. Beak, J. Am. Chem. Soc. 1992, 114, 9206-9207.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 9206-9207
    • Li, J.1    Beak, P.2
  • 57
    • 0347338363 scopus 로고
    • (Houben Weyl), 4th ed.; Thieme, Stuttgart
    • Counterions and polar solvent effects should favor the free alkoxide. for mechanisms of anion stabilization see: C. Lambert, P. v. R. Schleyer, Methoden Org. Chem. (Houben Weyl), 4th ed.; 1952-, Vol. E19d, Thieme, Stuttgart, 1993, p. 1.
    • (1952) Methoden Org. Chem. , vol.E19D , pp. 1
    • Lambert, C.1    Schleyer, P.V.R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.