메뉴 건너뛰기




Volumn 64, Issue 17, 1999, Pages 6169-6176

Synthesis of oxochromium(VI) alkoxides via epoxide cleavage. Structure, reactivity, and mechanism

Author keywords

[No Author keywords available]

Indexed keywords

BUTYLENE OXIDE; CHLOROHYDRIN DERIVATIVE; CHROMIUM DERIVATIVE; EPOXIDE; ETHYLENE OXIDE DERIVATIVE; OXOCHROMIUM; PROPYLENE OXIDE; UNCLASSIFIED DRUG;

EID: 0033588307     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982357f     Document Type: Article
Times cited : (6)

References (58)
  • 1
    • 33845278154 scopus 로고
    • Scriven, E. C. Chem. Rev. 1988, 88, 297; Bartók, M.; Láng, K. L. In Heterocyclic Compounds (Small Ring Heterocycles, Oxiranes); Hassner, A., Ed.; Wiley Interscience: New York, 1985; Part 3, Vol. 42. Somasekar, A. In Comprehensive Organic Synthesis (Addition Reactions with Formation of C-C Bonds); Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 7.
    • (1988) Chem. Rev. , vol.88 , pp. 297
    • Scriven, E.C.1
  • 2
    • 25944440883 scopus 로고
    • Hassner, A., Ed.; Wiley Interscience: New York
    • Scriven, E. C. Chem. Rev. 1988, 88, 297; Bartók, M.; Láng, K. L. In Heterocyclic Compounds (Small Ring Heterocycles, Oxiranes); Hassner, A., Ed.; Wiley Interscience: New York, 1985; Part 3, Vol. 42. Somasekar, A. In Comprehensive Organic Synthesis (Addition Reactions with Formation of C-C Bonds); Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 7.
    • (1985) Heterocyclic Compounds (Small ring Heterocycles, Oxiranes) , vol.42 , Issue.3 PART
    • Bartók, M.1    Láng, K.L.2
  • 3
    • 0003417469 scopus 로고
    • Trost, B. M., Ed.; Pergamon Press: New York
    • Scriven, E. C. Chem. Rev. 1988, 88, 297; Bartók, M.; Láng, K. L. In Heterocyclic Compounds (Small Ring Heterocycles, Oxiranes); Hassner, A., Ed.; Wiley Interscience: New York, 1985; Part 3, Vol. 42. Somasekar, A. In Comprehensive Organic Synthesis (Addition Reactions with Formation of C-C Bonds); Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 7.
    • (1991) Comprehensive Organic Synthesis (Addition Reactions with Formation of C-C Bonds) , vol.7
    • Somasekar, A.1
  • 6
    • 0004233837 scopus 로고
    • Thygarajan, B. S., Ed.; Wiley: New York
    • Buchanan, J. G.; Sable, H. Z. In Selective Organic Transformations; Thygarajan, B. S., Ed.; Wiley: New York, 1972; Vol. 1. Parker, B. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737. Rosowsky, A. In Heterocyclic compounds with three and four-membered Rings; Weissberger, A., Ed.; Wiley: New York, 1964; Part 1.
    • (1972) Selective Organic Transformations , vol.1
    • Buchanan, J.G.1    Sable, H.Z.2
  • 7
    • 33947470048 scopus 로고
    • Buchanan, J. G.; Sable, H. Z. In Selective Organic Transformations; Thygarajan, B. S., Ed.; Wiley: New York, 1972; Vol. 1. Parker, B. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737. Rosowsky, A. In Heterocyclic compounds with three and four-membered Rings; Weissberger, A., Ed.; Wiley: New York, 1964; Part 1.
    • (1959) Chem. Rev. , vol.59 , pp. 737
    • Parker, B.E.1    Isaacs, N.S.2
  • 8
    • 0345465855 scopus 로고
    • Weissberger, A., Ed.; Wiley: New York
    • Buchanan, J. G.; Sable, H. Z. In Selective Organic Transformations; Thygarajan, B. S., Ed.; Wiley: New York, 1972; Vol. 1. Parker, B. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737. Rosowsky, A. In Heterocyclic compounds with three and four-membered Rings; Weissberger, A., Ed.; Wiley: New York, 1964; Part 1.
    • (1964) Heterocyclic Compounds with Three and Four-membered Rings , Issue.1 PART
    • Rosowsky, A.1
  • 13
    • 0000377350 scopus 로고
    • Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768. Paterson, I.; Berrisford, D. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 1179.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 2768
    • Nugent, W.A.1
  • 17
    • 0345664754 scopus 로고
    • Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897. Leighton, J. L.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 389. Schaus, S. E.; Jacobsen, E. N. Tetrahedron Lett. 1996, 37, 7937. Larrow, J. F.; Schaus, S.E.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 7420.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 5897
    • Martinez, L.E.1    Leighton, J.L.2    Carsten, D.H.3    Jacobsen, E.N.4
  • 18
    • 0030070775 scopus 로고    scopus 로고
    • Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897. Leighton, J. L.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 389. Schaus, S. E.; Jacobsen, E. N. Tetrahedron Lett. 1996, 37, 7937. Larrow, J. F.; Schaus, S.E.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 7420.
    • (1996) J. Org. Chem. , vol.61 , pp. 389
    • Leighton, J.L.1    Jacobsen, E.N.2
  • 19
    • 0030605102 scopus 로고    scopus 로고
    • Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897. Leighton, J. L.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 389. Schaus, S. E.; Jacobsen, E. N. Tetrahedron Lett. 1996, 37, 7937. Larrow, J. F.; Schaus, S.E.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 7420.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 7937
    • Schaus, S.E.1    Jacobsen, E.N.2
  • 20
    • 0029757771 scopus 로고    scopus 로고
    • Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897. Leighton, J. L.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 389. Schaus, S. E.; Jacobsen, E. N. Tetrahedron Lett. 1996, 37, 7937. Larrow, J. F.; Schaus, S.E.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 7420.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 7420
    • Larrow, J.F.1    Schaus, S.E.2    Jacobsen, E.N.3
  • 22
    • 0002405607 scopus 로고
    • Olah, G. A., Ed.; Interscience: New York
    • Johnson, F. In Friedel-Crafts and related Reactions; Olah, G. A., Ed.; Interscience: New York, 1965; Vol. IV, p 1. Malinovskii, M. S. Epoxides and their Derivatives; Israel Program for scientific Translation, 1965. Dittus, G. In Houben-Weyl, Methoden der Organischen Chemie; Georg Thieme Verlag: Stuttgart, 1955; Vol. 6/3, p 437.
    • (1965) Friedel-Crafts and Related Reactions , vol.4 , pp. 1
    • Johnson, F.1
  • 23
    • 0344603758 scopus 로고
    • Israel Program for scientific Translation
    • Johnson, F. In Friedel-Crafts and related Reactions; Olah, G. A., Ed.; Interscience: New York, 1965; Vol. IV, p 1. Malinovskii, M. S. Epoxides and their Derivatives; Israel Program for scientific Translation, 1965. Dittus, G. In Houben-Weyl, Methoden der Organischen Chemie; Georg Thieme Verlag: Stuttgart, 1955; Vol. 6/3, p 437.
    • (1965) Epoxides and Their Derivatives
    • Malinovskii, M.S.1
  • 24
    • 0345034714 scopus 로고
    • Georg Thieme Verlag: Stuttgart
    • Johnson, F. In Friedel-Crafts and related Reactions; Olah, G. A., Ed.; Interscience: New York, 1965; Vol. IV, p 1. Malinovskii, M. S. Epoxides and their Derivatives; Israel Program for scientific Translation, 1965. Dittus, G. In Houben-Weyl, Methoden der Organischen Chemie; Georg Thieme Verlag: Stuttgart, 1955; Vol. 6/3, p 437.
    • (1955) Houben-Weyl, Methoden der Organischen Chemie , vol.6 , Issue.3 , pp. 437
    • Dittus, G.1
  • 31
    • 0344603759 scopus 로고    scopus 로고
    • note
    • 1H NMR signal (which is the averaged resonance of free ethylene oxide and species where it serves as a ligand) becomes more and more shifted and broadened and the integral perturbed as can be seen in Figure 1.
  • 32
    • 0344603756 scopus 로고    scopus 로고
    • note
    • 2Cl unit.
  • 33
    • 0344603757 scopus 로고    scopus 로고
    • note
    • 19 was considered as well.
  • 34
    • 0344172098 scopus 로고    scopus 로고
    • note
    • 2 at higher sample concentrations, so that the integration errors become larger in the second period of the reaction.
  • 38
    • 0344172093 scopus 로고    scopus 로고
    • note
    • To be accurate, all equilibria 2 is involved in would have to be considered, but in agreement with the experimental results it can be assumed that these quickly adjust and also that 2 is a major compound in solution. Moreover, neither reaction ii nor the decomposition processes were considered, but this should be appropriate for the first periods of the reactions.
  • 42
    • 0344603750 scopus 로고    scopus 로고
    • note
    • Plus enantiomers, which also form as the propylene oxide employed was not enantiomerically pure, but these of course have identical NMR properties.
  • 43
    • 37549004997 scopus 로고
    • Kristyán, S.; Pulay, P. Chem. Phys. Lett. 1994, 229, 175. Wright, T. C. J. Chem. Phys. 1996, 105, 7579. Pérez-Jordà, J. M.; Becke, A. D. Chem. Phys. Lett 1995, 233, 134. Ruiz, E.; Salahub, D. R.; Vela, A. J. Phys. Chem. 1996, 100, 12265. García, A.; Cruz, E. M.; Sarasola; C.; Ugalde, J. M. Phys. Phys. Chem. A 1997, 101, 3021.
    • (1994) Chem. Phys. Lett. , vol.229 , pp. 175
    • Kristyán, S.1    Pulay, P.2
  • 44
    • 0000567722 scopus 로고    scopus 로고
    • Kristyán, S.; Pulay, P. Chem. Phys. Lett. 1994, 229, 175. Wright, T. C. J. Chem. Phys. 1996, 105, 7579. Pérez-Jordà, J. M.; Becke, A. D. Chem. Phys. Lett 1995, 233, 134. Ruiz, E.; Salahub, D. R.; Vela, A. J. Phys. Chem. 1996, 100, 12265. García, A.; Cruz, E. M.; Sarasola; C.; Ugalde, J. M. Phys. Phys. Chem. A 1997, 101, 3021.
    • (1996) J. Chem. Phys. , vol.105 , pp. 7579
    • Wright, T.C.1
  • 45
    • 4243476736 scopus 로고
    • Kristyán, S.; Pulay, P. Chem. Phys. Lett. 1994, 229, 175. Wright, T. C. J. Chem. Phys. 1996, 105, 7579. Pérez-Jordà, J. M.; Becke, A. D. Chem. Phys. Lett 1995, 233, 134. Ruiz, E.; Salahub, D. R.; Vela, A. J. Phys. Chem. 1996, 100, 12265. García, A.; Cruz, E. M.; Sarasola; C.; Ugalde, J. M. Phys. Phys. Chem. A 1997, 101, 3021.
    • (1995) Chem. Phys. Lett , vol.233 , pp. 134
    • Pérez-Jordà, J.M.1    Becke, A.D.2
  • 46
    • 0030197702 scopus 로고    scopus 로고
    • Kristyán, S.; Pulay, P. Chem. Phys. Lett. 1994, 229, 175. Wright, T. C. J. Chem. Phys. 1996, 105, 7579. Pérez-Jordà, J. M.; Becke, A. D. Chem. Phys. Lett 1995, 233, 134. Ruiz, E.; Salahub, D. R.; Vela, A. J. Phys. Chem. 1996, 100, 12265. García, A.; Cruz, E. M.; Sarasola; C.; Ugalde, J. M. Phys. Phys. Chem. A 1997, 101, 3021.
    • (1996) J. Phys. Chem. , vol.100 , pp. 12265
    • Ruiz, E.1    Salahub, D.R.2    Vela, A.3
  • 47
    • 0001347790 scopus 로고    scopus 로고
    • Kristyán, S.; Pulay, P. Chem. Phys. Lett. 1994, 229, 175. Wright, T. C. J. Chem. Phys. 1996, 105, 7579. Pérez-Jordà, J. M.; Becke, A. D. Chem. Phys. Lett 1995, 233, 134. Ruiz, E.; Salahub, D. R.; Vela, A. J. Phys. Chem. 1996, 100, 12265. García, A.; Cruz, E. M.; Sarasola; C.; Ugalde, J. M. Phys. Phys. Chem. A 1997, 101, 3021.
    • (1997) Phys. Phys. Chem. A , vol.101 , pp. 3021
    • García, A.1    Cruz, E.M.2    Sarasola, C.3    Ugalde, J.M.4
  • 48
    • 0345034709 scopus 로고    scopus 로고
    • note
    • t in the form of two enantiomers which, however, naturally show the same NMR spectra.
  • 49
    • 0344603743 scopus 로고    scopus 로고
    • note
    • 1, but it would not be appropriate to try to deduce any information from their intensities.
  • 50
    • 0006542462 scopus 로고    scopus 로고
    • Limberg, C.; Köppe, R.; Schnöckel, H. Angew. Chem. 1998, 110, 512-515; Angew. Chem., Int. Ed. Engl. 1998, 37, 496-499. Limberg, C.; Köppe, R. Inorg. Chem. 1999, 38, 2106-2116.
    • (1998) Angew. Chem. , vol.110 , pp. 512-515
    • Limberg, C.1    Köppe, R.2    Schnöckel, H.3
  • 51
    • 0032473573 scopus 로고    scopus 로고
    • Limberg, C.; Köppe, R.; Schnöckel, H. Angew. Chem. 1998, 110, 512-515; Angew. Chem., Int. Ed. Engl. 1998, 37, 496-499. Limberg, C.; Köppe, R. Inorg. Chem. 1999, 38, 2106-2116.
    • (1998) Angew. Chem., Int. Ed. Engl. , vol.37 , pp. 496-499
  • 52
    • 0000265713 scopus 로고    scopus 로고
    • Limberg, C.; Köppe, R.; Schnöckel, H. Angew. Chem. 1998, 110, 512-515; Angew. Chem., Int. Ed. Engl. 1998, 37, 496-499. Limberg, C.; Köppe, R. Inorg. Chem. 1999, 38, 2106-2116.
    • (1999) Inorg. Chem. , vol.38 , pp. 2106-2116
    • Limberg, C.1    Köppe, R.2
  • 53
    • 0001090301 scopus 로고
    • Danopoulos, A. A.; Leung, Wa-Hung; Wilkinson, G.; Hussain-Bates, B.; Hursthouse, M. B. Polyhedron 1990, 9, 2625. Lam, HonWah, Wilkinson, G.; Hussain-Bates, B.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1993, 781. Cles, M. P. Dalby, C. I.; Gibson, V. C.; Clegg, W.; Elsegood, M. R. J. J. Chem. Soc., Chem. Commun. 1995, 1709. Leung, Wah-Hung; Wu, Man-Ching; Lau, Tai-Chu; Wong, Wing- Tak Inorg. Chem. 1995, 34, 4271. Meijboom, N.; Schaverien, C. J.; Orpen, A. G. Organometallics 1990, 9, 774. (33) The formation of 6 will also contribute to the deviations found for the later periods of the kinetic investigations.
    • (1990) Polyhedron , vol.9 , pp. 2625
    • Danopoulos, A.A.1    Leung, W.-H.2    Wilkinson, G.3    Hussain-Bates, B.4    Hursthouse, M.B.5
  • 54
    • 37049072602 scopus 로고
    • Danopoulos, A. A.; Leung, Wa-Hung; Wilkinson, G.; Hussain- Bates, B.; Hursthouse, M. B. Polyhedron 1990, 9, 2625. Lam, HonWah, Wilkinson, G.; Hussain-Bates, B.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1993, 781. Cles, M. P. Dalby, C. I.; Gibson, V. C.; Clegg, W.; Elsegood, M. R. J. J. Chem. Soc., Chem. Commun. 1995, 1709. Leung, Wah-Hung; Wu, Man-Ching; Lau, Tai-Chu; Wong, Wing- Tak Inorg. Chem. 1995, 34, 4271. Meijboom, N.; Schaverien, C. J.; Orpen, A. G. Organometallics 1990, 9, 774. (33) The formation of 6 will also contribute to the deviations found for the later periods of the kinetic investigations.
    • (1993) J. Chem. Soc., Dalton Trans. , pp. 781
    • Lam, H.1    Wilkinson, G.2    Hussain-Bates, B.3    Hursthouse, M.B.4
  • 55
    • 0344603740 scopus 로고
    • Danopoulos, A. A.; Leung, Wa-Hung; Wilkinson, G.; Hussain- Bates, B.; Hursthouse, M. B. Polyhedron 1990, 9, 2625. Lam, HonWah, Wilkinson, G.; Hussain-Bates, B.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1993, 781. Cles, M. P. Dalby, C. I.; Gibson, V. C.; Clegg, W.; Elsegood, M. R. J. J. Chem. Soc., Chem. Commun. 1995, 1709. Leung, Wah-Hung; Wu, Man-Ching; Lau, Tai-Chu; Wong, Wing- Tak Inorg. Chem. 1995, 34, 4271. Meijboom, N.; Schaverien, C. J.; Orpen, A. G. Organometallics 1990, 9, 774. (33) The formation of 6 will also contribute to the deviations found for the later periods of the kinetic investigations.
    • (1995) J. Chem. Soc., Chem. Commun. , pp. 1709
    • Cles, M.P.1    Dalby, C.I.2    Gibson, V.C.3    Clegg, W.4    Elsegood, M.R.J.5
  • 56
    • 0001002934 scopus 로고
    • Danopoulos, A. A.; Leung, Wa-Hung; Wilkinson, G.; Hussain- Bates, B.; Hursthouse, M. B. Polyhedron 1990, 9, 2625. Lam, HonWah, Wilkinson, G.; Hussain-Bates, B.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1993, 781. Cles, M. P. Dalby, C. I.; Gibson, V. C.; Clegg, W.; Elsegood, M. R. J. J. Chem. Soc., Chem. Commun. 1995, 1709. Leung, Wah-Hung; Wu, Man-Ching; Lau, Tai-Chu; Wong, Wing-Tak Inorg. Chem. 1995, 34, 4271. Meijboom, N.; Schaverien, C. J.; Orpen, A. G. Organometallics 1990, 9, 774. (33) The formation of 6 will also contribute to the deviations found for the later periods of the kinetic investigations.
    • (1995) Inorg. Chem. , vol.34 , pp. 4271
    • Leung, W.-H.1    Wu, M.-C.2    Lau, T.-C.3    Wong, W.-T.4
  • 57
    • 0025401382 scopus 로고
    • Danopoulos, A. A.; Leung, Wa-Hung; Wilkinson, G.; Hussain- Bates, B.; Hursthouse, M. B. Polyhedron 1990, 9, 2625. Lam, HonWah, Wilkinson, G.; Hussain-Bates, B.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1993, 781. Cles, M. P. Dalby, C. I.; Gibson, V. C.; Clegg, W.; Elsegood, M. R. J. J. Chem. Soc., Chem. Commun. 1995, 1709. Leung, Wah-Hung; Wu, Man-Ching; Lau, Tai-Chu; Wong, Wing- Tak Inorg. Chem. 1995, 34, 4271. Meijboom, N.; Schaverien, C. J.; Orpen, A. G. Organometallics 1990, 9, 774. (33) The formation of 6 will also contribute to the deviations found for the later periods of the kinetic investigations.
    • (1990) Organometallics , vol.9 , pp. 774
    • Meijboom, N.1    Schaverien, C.J.2    Orpen, A.G.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.