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Volumn , Issue 4, 2005, Pages 572-576

A comment on the Gurjar mechanism for alkene isomerization using the Grubbs olefin metathesis catalysts

Author keywords

Allylic alcohol; Atom transfer; Grubbs; Isomerization; Mechanism; Metathesis

Indexed keywords

ALKENE; ALLYL ALCOHOL;

EID: 15444367668     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-862384     Document Type: Article
Times cited : (33)

References (84)
  • 6
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    • For sporadic reports of olefin isomerisation using catalysts such as 1a and 1b see: (a) Kotha, S.; Mandal, K. Tetrahedron Lett. 2004, 45, 1391.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 1391
    • Kotha, S.1    Mandal, K.2
  • 25
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    • note
    • 11
  • 26
    • 0001557958 scopus 로고
    • 12 β-H eliminations in related iridium complexes also proceed via cleavage of an endocyclic C-H bond. See: Fryzuk, M. D.; Gao, X.; Rettig, S. J. J. Am. Chem. Soc. 1995, 117, 3106.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 3106
    • Fryzuk, M.D.1    Gao, X.2    Rettig, S.J.3
  • 28
  • 45
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    • (b) Trichloroacetate 2c was prepared from 2-cyclohenen-1-ol-1-d (having >98% d-incorporation at C-1). See: Goering, H. L.; Paisley, S. D. J. Org. Chem. 1987, 52, 943.
    • (1987) J. Org. Chem. , vol.52 , pp. 943
    • Goering, H.L.1    Paisley, S.D.2
  • 46
    • 15444372763 scopus 로고    scopus 로고
    • note
    • (c) We have yet to rule out the possibility that this 'isomerization' reaction might proceed via an elimination-intermolecular Kharasch sequence. Experiments are in hand to differentiate between these alternate pathways.
  • 55
    • 0141841782 scopus 로고    scopus 로고
    • (b) The in situ generation of hydrido ruthenium complexes, which are themselves catalysts for olefin isomerization, has been reported. See: Schmidt, B.; Pohler, M. Org. Biomol. Chem. 2003, 1, 2512.
    • (2003) Org. Biomol. Chem. , vol.1 , pp. 2512
    • Schmidt, B.1    Pohler, M.2
  • 56
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    • and references therein
    • (c) Schmidt, B. Chem. Commun. 2004, 742; and references therein.
    • (2004) Chem. Commun. , vol.742
    • Schmidt, B.1
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    • note
    • 2 and NaOH in the presence of post-metathesis catalyst.
  • 62
    • 0034859403 scopus 로고    scopus 로고
    • (c) Grée has reported that various hydrido ruthenium complexes effect the same isomerization reaction albeit with much higher levels of deuterium incorporation (up to 90% retention). The degree of d-incorporation is ligand dependent. We thank Prof. Grée for spectral data of 12a. See: Uma, R.; Davies, M. K.; Crévisy, C.; Grée, R. Eur. J. Org. Chem. 2001, 3141.
    • (2001) Eur. J. Org. Chem. , pp. 3141
    • Uma, R.1    Davies, M.K.2    Crévisy, C.3    Grée, R.4
  • 76
    • 1242307300 scopus 로고    scopus 로고
    • Schmidt has recently reported the partitioning of reactivity between the complexes 1a and 1b in RCM/ATRC reactions. In keeping with our results these workers found that the more robust second generation catalyst, 1b, did not catalyze effectively ATRC reactions. See: Schmidt, B.; Pohler, M.; Costisella, B. J. Org. Chem. 2004, 69, 1421.
    • (2004) J. Org. Chem. , vol.69 , pp. 1421
    • Schmidt, B.1    Pohler, M.2    Costisella, B.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.