메뉴 건너뛰기




Volumn 27, Issue 20, 2008, Pages 5353-5360

Reactions of an (arylimido)vanadium(v)-alkylidene, V(CHSiMe 3)(N-2,6-Me2C6H3)(N=C tBu2)(PMe3), with nitriles, diphenylacetylene, and styrene

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTALLOGRAPHY; CYANIDES; STYRENE; TRANSITION METALS; VANADIUM ALLOYS; X RAY CRYSTALLOGRAPHY;

EID: 55249106697     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800479u     Document Type: Article
Times cited : (50)

References (68)
  • 1
    • 0033750822 scopus 로고    scopus 로고
    • For examples, see: a
    • For examples, see: (a) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565.
    • (2000) Chem. Rev , vol.100 , pp. 1565
    • Buchmeiser, M.R.1
  • 2
    • 1442360753 scopus 로고    scopus 로고
    • Grubbs, R. H, Ed, Wiley-VCH: Weinheim, Germany, Vols
    • (b) Grubbs, R. H., Ed. Handbook of Metathesis; Wiley-VCH: Weinheim, Germany, 2003; Vols. 1-3.
    • (2003) Handbook of Metathesis , vol.1-3
  • 4
    • 45049085143 scopus 로고    scopus 로고
    • Imamoglu, Y, Dragutan, V, Eds, Springer: Dordrecht, The Netherlands
    • (d) Imamoglu, Y., Dragutan, V., Eds. Metathesis Chemistry; Springer: Dordrecht, The Netherlands, 2007.
    • (2007) Metathesis Chemistry
  • 5
    • 0001422883 scopus 로고
    • For examples, see: a
    • For examples, see: (a) Schrock, R. R. Acc. Chem. Res. 1990, 23, 158.
    • (1990) Acc. Chem. Res , vol.23 , pp. 158
    • Schrock, R.R.1
  • 6
    • 55249111192 scopus 로고    scopus 로고
    • Schrock, R. R. In Alkene Metathesis in Organic Synthesis; Fürstner, A.,Ed.; Springer: Berlin, Germany, 1998; p 1.
    • (b) Schrock, R. R. In Alkene Metathesis in Organic Synthesis; Fürstner, A.,Ed.; Springer: Berlin, Germany, 1998; p 1.
  • 7
    • 14644441385 scopus 로고    scopus 로고
    • Grubbs, R. H, Ed, Wiley-VCH: Weinheim, Germany
    • (c) Schrock, R. R. In Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, Germany, 2003; Vol. 1, p 8.
    • (2003) Handbook of Metathesis , vol.1 , pp. 8
    • Schrock, R.R.1
  • 9
    • 9944235571 scopus 로고    scopus 로고
    • GrubbsR. H, Ed, Wiley-VCH: Weinheim
    • (b) Nguyen, S. T.; Trnka, T. M. In Handbook of Metathesis; GrubbsR. H., Ed.; Wiley-VCH: Weinheim, 2003; Vol. 3, pp 61-85.
    • (2003) Handbook of Metathesis , vol.3 , pp. 61-85
    • Nguyen, S.T.1    Trnka, T.M.2
  • 10
    • 33845559693 scopus 로고
    • For examples, see: a
    • For examples, see: (a) Schrock, R. R. Acc. Chem. Res. 1979, 12, 98.
    • (1979) Acc. Chem. Res , vol.12 , pp. 98
    • Schrock, R.R.1
  • 14
    • 33845375542 scopus 로고
    • For example (pioneering examples in titanium, see: a
    • For example (pioneering examples in titanium), see: (a) Gilliom, L. R.; Grubbs, R. H. J. Am. Chem. Soc. 1986, 108, 733.
    • (1986) J. Am. Chem. Soc , vol.108 , pp. 733
    • Gilliom, L.R.1    Grubbs, R.H.2
  • 15
    • 55249086181 scopus 로고    scopus 로고
    • The role of the 'Tebbe complex in olefin metathesis: Grubbs, R. H. In Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, Germany, 2003; l, p 4.
    • (b) The role of the 'Tebbe complex" in olefin metathesis: Grubbs, R. H. In Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, Germany, 2003; Vol. l, p 4.
  • 16
    • 33947093052 scopus 로고    scopus 로고
    • Pioneering work concerning the so-called Tebbe reagent (c-e): Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611.
    • (c) Pioneering work concerning the so-called Tebbe reagent (c-e): Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611.
  • 19
    • 0000504676 scopus 로고
    • Examples:(a) Carrick, W. L
    • Examples:(a) Carrick, W. L. J. Am. Chem. Soc. 1958, 80, 6455.
    • (1958) J. Am. Chem. Soc , vol.80 , pp. 6455
  • 26
    • 33645800018 scopus 로고    scopus 로고
    • Bevy, L. P, Ed, NOVA Science Publishers: New York
    • (d) Nomura, K. In New Developments in Catalysis Research; Bevy, L. P., Ed.; NOVA Science Publishers: New York, 2005; p 199.
    • (2005) New Developments in Catalysis Research , pp. 199
    • Nomura, K.1
  • 27
    • 0000661211 scopus 로고    scopus 로고
    • Examples of isolation of terminal vanadium(III),(IV) alkylidenes: (a) Hessen, B.; Meetsma, A.; Teuben, J. H. J. Am. Chem. Soc. 1989, 111, 5977.
    • Examples of isolation of terminal vanadium(III),(IV) alkylidenes: (a) Hessen, B.; Meetsma, A.; Teuben, J. H. J. Am. Chem. Soc. 1989, 111, 5977.
  • 32
    • 0001559505 scopus 로고    scopus 로고
    • Examples of isolation of terminal vanadium(V) - alkylidenes: (a) Buijink, J.-K. F.; Teuben, J. H.; Kooijman, H.; Spek, A. L. Organometallics 1994, 13, 2922 No reaction between CpV(CHPh)(NAr)(PMe3) and norbomene or acetone was observed.
    • Examples of isolation of terminal vanadium(V) - alkylidenes: (a) Buijink, J.-K. F.; Teuben, J. H.; Kooijman, H.; Spek, A. L. Organometallics 1994, 13, 2922 No reaction between CpV(CHPh)(NAr)(PMe3) and norbomene or acetone was observed.
  • 35
    • 0000856941 scopus 로고    scopus 로고
    • Examples of related complexes containing vanadium(V)-carbon double bonds:(a) Hessen, B.; Meetsma, A.; van Bolhuis, F.; Teuben, J. H. Organometallics 1990, 9, 1925.
    • Examples of related complexes containing vanadium(V)-carbon double bonds:(a) Hessen, B.; Meetsma, A.; van Bolhuis, F.; Teuben, J. H. Organometallics 1990, 9, 1925.
  • 41
    • 55249100649 scopus 로고    scopus 로고
    • These results were partly presented at the XVIIth International symposium on olefin metathesis (ISOMXVII), July2007, Pasadena, CA.
    • These results were partly presented at the XVIIth International symposium on olefin metathesis (ISOMXVII), July2007, Pasadena, CA.
  • 46
    • 55249112170 scopus 로고    scopus 로고
    • The NMR spectra for 1 and the spectra monitoring the reaction of 1 with RCN (and with styrene) are shown in the Supporting Information.
    • The NMR spectra for 1 and the spectra monitoring the reaction of 1 with RCN (and with styrene) are shown in the Supporting Information.
  • 47
    • 55249105094 scopus 로고    scopus 로고
    • Two possibilities, i) partial dissociation of PMe3 (as observed in the alkylidene recently reported)12 and (ii) a mixture of isomers (syn/anti isomers, as seen in the molybdenum-alkylidene complexes),2,4b have to be considered for explanation for the two resonances in the 51V NMR spectra of 1. PMe3 in the aryloxo-alkylidene V(CHSiMe3)(N-2,6-Me2C6H 3, O-iPr2C6H3)(PMe 3) dissociated partially, confirmed by both the elemental analysis and the NMR spectra,12 and the 1H NMR spectrum of 1 (in C6D6) showed only one broad resonance ascribed to the alkylidene proton and only one broad resonance ascribed to the alkylidene was observed in the 13C NMR spectrum (and one broad resonance was seen in the 31P NMR spectrum, The latter possibility the presence of isomers, shown
    • 3 are shown in the Supporting Information.
  • 48
    • 33947094577 scopus 로고    scopus 로고
    • Selected examples for reaction with nitriles (Ta): (a) Schrock, R. R.; Fellmann, J. D. J. Am. Chem. Soc. 1978, 100, 3359-3370.
    • Selected examples for reaction with nitriles (Ta): (a) Schrock, R. R.; Fellmann, J. D. J. Am. Chem. Soc. 1978, 100, 3359-3370.
  • 51
    • 0000356919 scopus 로고    scopus 로고
    • Selected examples for reaction with nitriles (Ti): (a) Doxsee, K. M.; Farahi, J. B.; Hope, H. J. Am. Chem. Soc. 1991, 113, 8889.
    • Selected examples for reaction with nitriles (Ti): (a) Doxsee, K. M.; Farahi, J. B.; Hope, H. J. Am. Chem. Soc. 1991, 113, 8889.
  • 54
    • 55249083867 scopus 로고    scopus 로고
    • Detailed analysis parameters including CIF files are shown in the Supporting Information
    • Detailed analysis parameters including CIF files are shown in the Supporting Information.
  • 58
    • 33847801002 scopus 로고    scopus 로고
    • Bimolecular decomposition of Cp2Ta(CH2)(CH 3) in the presence of PMe3 afforded Cp2Ta(V, CH2CH2)(CH3) and Cp2Ta(CH 3)(PMe3, a) Schrock, R. R J. Am. Chem. Soc. 1975, 97, 6577
    • 3): (a) Schrock, R. R J. Am. Chem. Soc. 1975, 97, 6577.
  • 61
    • 2442547607 scopus 로고    scopus 로고
    • Formation of Mo(NAi′)(Biphen)(ethylene) complex from Mo(NAr′)(CHCMe2Ph)(Biphen) by reacting with 2 equiv of ethylene via β-H elimination: (a) Tsang, W. C. P, Jamieson, J. Y, Aeilts, S. L, Hultzsch, K. C, Schrock, R. R, Hoveyda, A. H. Organometallics 2004, 23, 1997. In our case, we would be able to eliminate this possibility [a route via formation of vanadium(III) and subsequent addition of styrène, because the observed reaction product by 51V NMR spectrum14 from the reaction of 1 with 1 equiv of styrene was 6 exclusively. The related reaction in CpTi(CHMe3)[PMe 2-CH2C(O)-CMe2-o-C6H 4CMe2, The titanium-alkylidene reacts with ethylene, initially forming a metallacycle, while subsequent reactions produce a stable ethylene complex
    • 2] (The titanium-alkylidene reacts with ethylene, initially forming a metallacycle, while subsequent reactions produce a stable ethylene complex).
  • 65
    • 55249098295 scopus 로고    scopus 로고
    • Negligible amount of polymer was collected when a toluene solution (5 mL) containing complex 6 (5 mg, 10 μmol) and norbornene 200 mg (2.1 mmol) was heated at 80 °C for 1 h.
    • Negligible amount of polymer was collected when a toluene solution (5 mL) containing complex 6 (5 mg, 10 μmol) and norbornene 200 mg (2.1 mmol) was heated at 80 °C for 1 h.
  • 66
    • 55249126723 scopus 로고    scopus 로고
    • DIRDIF94: Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; de Delder, R.; Israel, R.; Smits, J. M. M. The DIRDIF94 program system, Technical report of crystallography laboratory; University of Nijmegen: The Netherlands, 1994.
    • DIRDIF94: Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; de Delder, R.; Israel, R.; Smits, J. M. M. The DIRDIF94 program system, Technical report of crystallography laboratory; University of Nijmegen: The Netherlands, 1994.
  • 67
    • 34047252798 scopus 로고    scopus 로고
    • Crystal Structure Analysis Package; Rigaku and Rigaku/MSC: The Woodlands, TX
    • (a) Crystal Structure 3.6.0: Crystal Structure Analysis Package; Rigaku and Rigaku/MSC: The Woodlands, TX. 2000-2004.
    • (2000) Crystal Structure 3.6.0


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.