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Volumn , Issue 16, 2003, Pages 3147-3152

Reactions of a stable (phosphanyl)(silyl)carbene with aliphatic aldehydes: [2+1] versus [2+2] addition to a carbonyl group

Author keywords

Carbenes; Cycloadditions; Oxiranes; Phosphorus

Indexed keywords

(PHOSPHANYL)(SILYL)CARBENE; ALDEHYDE; ALKENE; ALKYL GROUP; CARBENE; CARBONYL DERIVATIVE; ETHYLENE OXIDE; PHOSPHORANE DERIVATIVE; PHOSPHORUS DERIVATIVE; SILICON DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0042978711     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300226     Document Type: Article
Times cited : (24)

References (47)
  • 8
    • 0033052250 scopus 로고    scopus 로고
    • [4a] For a review on the synthesis of 1,2-epoxyalkylphosphonates, see: B. Iorga, F. Eymery, P. Savignac, Synthesis 1999, 207. [4b] F. Hammerschmidt, Angew. Chem. Int. Ed. Engl. 1994, 33, 341. [4c] P. Liu, K. Murakami, T. Seki, X. He, S.-M. Yeung, T. Kuzuyama, H. Seto, H.-W. Liu, J. Am. Chem. Soc. 2001, 123, 4619.
    • (1999) Synthesis , pp. 207
    • Iorga, B.1    Eymery, F.2    Savignac, P.3
  • 9
    • 0027966348 scopus 로고
    • [4a] For a review on the synthesis of 1,2-epoxyalkylphosphonates, see: B. Iorga, F. Eymery, P. Savignac, Synthesis 1999, 207. [4b] F. Hammerschmidt, Angew. Chem. Int. Ed. Engl. 1994, 33, 341. [4c] P. Liu, K. Murakami, T. Seki, X. He, S.-M. Yeung, T. Kuzuyama, H. Seto, H.-W. Liu, J. Am. Chem. Soc. 2001, 123, 4619.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 341
    • Hammerschmidt, F.1
  • 11
    • 0000936734 scopus 로고
    • For a review on ylide formation from transient carbenes, see: A. Padwa, S. F. Hornbuckle, Chem. Rev. 1991, 91, 263.
    • (1991) Chem. Rev. , vol.91 , pp. 263
    • Padwa, A.1    Hornbuckle, S.F.2
  • 14
    • 0032723198 scopus 로고    scopus 로고
    • For recent reviews on N-heterocyclic carbenes, see: [7a] A. J. Arduengo III, Acc. Chem. Res. 1999, 32, 913. [7b] D. Bourissou, O. Guerret, F. P. Gabbai, G. Bertrand, Chem. Rev. 2000, 100, 39. [7c] W. A. Herrmann, T. Weskamp, V. P. W. Bohm, Adv. Organomet. Chem. 2001, 48, 1. [7d] L. Jafarpour, S. P. Nolan, Adv. Organomet. Chem. 2001, 46, 181. [7e] Herrmann, W. A, Angew. Chem. Int. Ed. 2002, 41, 1290.
    • (1999) Acc. Chem. Res. , vol.32 , pp. 913
    • Arduengo A.J. III1
  • 15
    • 0002138516 scopus 로고    scopus 로고
    • For recent reviews on N-heterocyclic carbenes, see: [7a] A. J. Arduengo III, Acc. Chem. Res. 1999, 32, 913. [7b] D. Bourissou, O. Guerret, F. P. Gabbai, G. Bertrand, Chem. Rev. 2000, 100, 39. [7c] W. A. Herrmann, T. Weskamp, V. P. W. Bohm, Adv. Organomet. Chem. 2001, 48, 1. [7d] L. Jafarpour, S. P. Nolan, Adv. Organomet. Chem. 2001, 46, 181. [7e] Herrmann, W. A, Angew. Chem. Int. Ed. 2002, 41, 1290.
    • (2000) Chem. Rev. , vol.100 , pp. 39
    • Bourissou, D.1    Guerret, O.2    Gabbai, F.P.3    Bertrand, G.4
  • 16
    • 33644888452 scopus 로고    scopus 로고
    • For recent reviews on N-heterocyclic carbenes, see: [7a] A. J. Arduengo III, Acc. Chem. Res. 1999, 32, 913. [7b] D. Bourissou, O. Guerret, F. P. Gabbai, G. Bertrand, Chem. Rev. 2000, 100, 39. [7c] W. A. Herrmann, T. Weskamp, V. P. W. Bohm, Adv. Organomet. Chem. 2001, 48, 1. [7d] L. Jafarpour, S. P. Nolan, Adv. Organomet. Chem. 2001, 46, 181. [7e] Herrmann, W. A, Angew. Chem. Int. Ed. 2002, 41, 1290.
    • (2001) Adv. Organomet. Chem. , vol.48 , pp. 1
    • Herrmann, W.A.1    Weskamp, T.2    Bohm, V.P.W.3
  • 17
    • 35448936556 scopus 로고    scopus 로고
    • For recent reviews on N-heterocyclic carbenes, see: [7a] A. J. Arduengo III, Acc. Chem. Res. 1999, 32, 913. [7b] D. Bourissou, O. Guerret, F. P. Gabbai, G. Bertrand, Chem. Rev. 2000, 100, 39. [7c] W. A. Herrmann, T. Weskamp, V. P. W. Bohm, Adv. Organomet. Chem. 2001, 48, 1. [7d] L. Jafarpour, S. P. Nolan, Adv. Organomet. Chem. 2001, 46, 181. [7e] Herrmann, W. A, Angew. Chem. Int. Ed. 2002, 41, 1290.
    • (2001) Adv. Organomet. Chem. , vol.46 , pp. 181
    • Jafarpour, L.1    Nolan, S.P.2
  • 18
    • 0037090932 scopus 로고    scopus 로고
    • For recent reviews on N-heterocyclic carbenes, see: [7a] A. J. Arduengo III, Acc. Chem. Res. 1999, 32, 913. [7b] D. Bourissou, O. Guerret, F. P. Gabbai, G. Bertrand, Chem. Rev. 2000, 100, 39. [7c] W. A. Herrmann, T. Weskamp, V. P. W. Bohm, Adv. Organomet. Chem. 2001, 48, 1. [7d] L. Jafarpour, S. P. Nolan, Adv. Organomet. Chem. 2001, 46, 181. [7e] Herrmann, W. A, Angew. Chem. Int. Ed. 2002, 41, 1290.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 1290
    • Herrmann, W.A.1
  • 28
    • 0042289310 scopus 로고    scopus 로고
    • note
    • In the case of benzaldehyde the corresponding thioxophosphoranyl oxirane has also been crystallized, and an X-ray diffraction study showed the same diastereoselectivity, contrary to the first attribution based on the NMR spectroscopic data. [10]
  • 32
    • 0042790428 scopus 로고    scopus 로고
    • note
    • P-C = 1.532 Å, C-Si = 1.795 Å, P-C-Si = 152.6°. See ref.[16]
  • 34
    • 0042790427 scopus 로고    scopus 로고
    • note
    • The energies of the HOMO and LUMO of 2′ are - 0.1905 and -0.0151 a. u, whereas the energies of acetaldehyde π and π* orbitals are -0.3644 and -0.0218 a. u., respectively.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.