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Volumn 11, Issue 9, 2007, Pages 741-772

Nitrile ylides: Generation, properties and synthetic applications

Author keywords

Azirines; Carbenoids; Dehydrochlorination; Dimerization; Heterocycles; Protonation

Indexed keywords

CYANIDES; DIMERIZATION; ORGANIC COMPOUNDS; SYNTHESIS (CHEMICAL);

EID: 34347266208     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527207780831710     Document Type: Review
Times cited : (21)

References (298)
  • 6
    • 0000629986 scopus 로고
    • Trost, B. M, Fleming, I, Ed, Pergamon Press: Oxford, &
    • (f) Padwa, A. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Ed.; Pergamon Press: Oxford, 1991; Vol. 4, pp. 1069-1109 & 1110-1168;
    • (1991) Comprehensive Organic Synthesis , vol.4
    • Padwa, A.1
  • 10
    • 85195239276 scopus 로고
    • Methoden Org. Chem, Houben-Weyl, Thieme
    • (c) Claus, P. K. In Methoden Org. Chem. (Houben-Weyl), Thieme, 1990, E14b/Teil 1, pp. 15-17;
    • (1990) E14b/Teil 1 , pp. 15-17
    • Claus, P.K.1
  • 21
    • 85195238737 scopus 로고    scopus 로고
    • See also a correction in
    • (b) See also a correction in J. Phys. Chem. A, 2001, 105, 9624.
    • (2001) , vol.9624 , Issue.105
    • Phys, J.1    Chem, A.2
  • 22
    • 34047148155 scopus 로고
    • Katrizky, A. R, Meth-Cohn, O, Rees, C. W, Eds, Elsevier: Oxford
    • (a) Paton, R. M. In omprehensive Organic Functional Group Transformations, Katrizky, A. R.; Meth-Cohn, O.; Rees, C. W., Eds.; Elsevier: Oxford, 1995, Vol. 3, pp. 677-692;
    • (1995) In omprehensive Organic Functional Group Transformations , vol.3 , pp. 677-692
    • Paton, R.M.1
  • 24
    • 85195241750 scopus 로고    scopus 로고
    • In Science of Synthesis
    • (c) Kanemasa, S. In Science of Synthesis, Thieme, 2005; Vol. 19, pp 67-78;
    • (2005) Thieme , vol.19 , pp. 67-78
    • Kanemasa, S.1
  • 34
    • 85195238065 scopus 로고    scopus 로고
    • See also reference 5
    • See also reference 5.
  • 54
    • 85195241789 scopus 로고    scopus 로고
    • Claus, P. K. In Methoden Org. Chem. (Houben-Weyl), Thieme, 1990, E14b/Teil 1, pp. 8-11.
    • Claus, P. K. In Methoden Org. Chem. (Houben-Weyl), Thieme, 1990, E14b/Teil 1, pp. 8-11.
  • 73
    • 85195242237 scopus 로고    scopus 로고
    • See also reference 19b
    • See also reference 19b.
  • 77
    • 0004278888 scopus 로고
    • Clarke, H. T, Johnson, J. R, Robinson, R, Ed, Princeton University Press: Princenton, NJ USA
    • Cornforth, J. W. In The Chemistry of Penicillin; Clarke, H. T.; Johnson, J. R.; Robinson, R., Ed.; Princeton University Press: Princenton, NJ (USA), 1949; p. 700.
    • (1949) The Chemistry of Penicillin , pp. 700
    • Cornforth, J.W.1
  • 90
    • 85195241951 scopus 로고    scopus 로고
    • The normal pathway for thermally induced cleavage of 2H-azirines is CN bond rupture. It has been shown that CC bond rupture can also occur thermally, but leading to different products from those obtained by photochemical reaction. See, (a) Wendling, L. A.; Bergman, R. G. J. Org. Chem., 1976, 41, 831 and references therein;
    • The normal pathway for thermally induced cleavage of 2H-azirines is CN bond rupture. It has been shown that CC bond rupture can also occur thermally, but leading to different products from those obtained by photochemical reaction. See, (a) Wendling, L. A.; Bergman, R. G. J. Org. Chem., 1976, 41, 831 and references therein;
  • 118
    • 85195236630 scopus 로고    scopus 로고
    • Referencia 25a; (b) Kitamura, T.; Kobayashi, S.; Taniguchi, H. J. Org. Chem., 1984, 49, 4755
    • (a) Referencia 25a; (b) Kitamura, T.; Kobayashi, S.; Taniguchi, H. J. Org. Chem., 1984, 49, 4755
  • 141
    • 85195238441 scopus 로고    scopus 로고
    • See also references 46c,d
    • See also references 46c,d.
  • 167
    • 85195238920 scopus 로고    scopus 로고
    • Tsuge, O.; Kanemasa, S.; Matsuda, K. J. Org. Chem., 1986, 51, 1997. It is also possible to generate azomethine ylides as nitrile ylide equivalents from N-(stannylmethyl)thioamides.
    • (b) Tsuge, O.; Kanemasa, S.; Matsuda, K. J. Org. Chem., 1986, 51, 1997. It is also possible to generate azomethine ylides as nitrile ylide equivalents from N-(stannylmethyl)thioamides.
  • 213
    • 85195242354 scopus 로고    scopus 로고
    • reference 45b
    • (b) reference 45b
  • 220
    • 85195237161 scopus 로고    scopus 로고
    • Padwa, A.; Rasmussen, J. K.; Tremper, A. J. Chem. Soc. Chem. Commun., 1976, 10. See also reference 82c.
    • Padwa, A.; Rasmussen, J. K.; Tremper, A. J. Chem. Soc. Chem. Commun., 1976, 10. See also reference 82c.
  • 223
    • 85195241834 scopus 로고    scopus 로고
    • Nguyen, M. T.; Ha, T.-K. J. Chem. Soc. Perkin Trans. 2, 1984, 1401. See also reference 3a.
    • (b) Nguyen, M. T.; Ha, T.-K. J. Chem. Soc. Perkin Trans. 2, 1984, 1401. See also reference 3a.
  • 226
    • 85195236303 scopus 로고    scopus 로고
    • Dietliker, K.; Gilgen, P.; Heimgartner, H.; Schmid, H. Helv. Chim. Acta, 1976, 59, 2074. See also references 23i and 39b.
    • (c) Dietliker, K.; Gilgen, P.; Heimgartner, H.; Schmid, H. Helv. Chim. Acta, 1976, 59, 2074. See also references 23i and 39b.
  • 230
    • 85195241839 scopus 로고    scopus 로고
    • Doyle, K. J.; Moody, C. J. Tetrahedron, 1994, 50, 3761. For an alternative mechanism see reference 52i.
    • Doyle, K. J.; Moody, C. J. Tetrahedron, 1994, 50, 3761. For an alternative mechanism see reference 52i.
  • 243
    • 85195239140 scopus 로고    scopus 로고
    • Claus, P. K. In Methoden Org. Chem. (Houben-Weyl), Thieme, 1990, E14b/Teil 1, pp. 20-33.
    • Claus, P. K. In Methoden Org. Chem. (Houben-Weyl), Thieme, 1990, E14b/Teil 1, pp. 20-33.
  • 244
    • 0002549529 scopus 로고
    • For an account on this controversy, see: a
    • For an account on this controversy, see: (a) Houk, K. N.; González, J.; Li, Y. Acc. Chem. Res., 1995, 28, 81.
    • (1995) Acc. Chem. Res , vol.28 , pp. 81
    • Houk, K.N.1    González, J.2    Li, Y.3
  • 245
    • 33947317869 scopus 로고
    • See, also: b
    • See, also: (b) Firestone, R. A. J. Org. Chem., 1968, 33, 2285
    • (1968) J. Org. Chem , vol.33 , pp. 2285
    • Firestone, R.A.1
  • 259
    • 85195242964 scopus 로고    scopus 로고
    • It has also been suggested that 1,1-cycloaddition of nitrile ylides is concerted and that the diradical is a secondary photoproduct, only formed when the nitrile ylide is generated photochemically. See, (a) Fischer, J.; Steglich, W. Angew. Chem. Int. Ed. Engl., 1979, 18, 167
    • It has also been suggested that 1,1-cycloaddition of nitrile ylides is concerted and that the diradical is a secondary photoproduct, only formed when the nitrile ylide is generated photochemically. See, (a) Fischer, J.; Steglich, W. Angew. Chem. Int. Ed. Engl., 1979, 18, 167
  • 264
    • 85195240300 scopus 로고    scopus 로고
    • For example, 1-octene or cyclohexene fail to add to nitrile ylides. However, the strained norbornene undergo cycloaddition, see reference 78b.
    • For example, 1-octene or cyclohexene fail to add to nitrile ylides. However, the strained norbornene undergo cycloaddition, see reference 78b.
  • 282
    • 0001388325 scopus 로고
    • For a review on reactions of heteroaromatics with nitrilium betaines, see
    • For a review on reactions of heteroaromatics with nitrilium betaines, see: Corsaro, A.; Pistarà, V. Trends Heterocycl. Chem., 1995, 4, 169.
    • (1995) Trends Heterocycl. Chem , vol.4 , pp. 169
    • Corsaro, A.1    Pistarà, V.2
  • 286
    • 85195239179 scopus 로고    scopus 로고
    • See also pages 1141 in reference 1f
    • (b) See also pages 1141 in reference 1f.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.