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Volumn 9, Issue 4, 2003, Pages 1000-1007

Evidence for the intermediacy of arylbenzylnitrenium ions in the thermal rearrangement of isoxazolidines derived from C,N-diarylnitrones and 2-morpholin-4-yl-acrylonitrile

Author keywords

Alkenes; Captodative alkenes; Electrophilic reactions; Nitrenium ions; Rearrangement

Indexed keywords

BENZENE; CHEMICAL ENGINEERING; THERMAL EFFECTS;

EID: 0037450110     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200390102     Document Type: Article
Times cited : (14)

References (42)
  • 1
    • 0028705750 scopus 로고
    • (Eds.: K. Hemminki, A. Dipple, D. E. G. Shuker, F. F. Kadlubar, D. Segerbäck, H. Bartsch), Oxford University Press. Oxford (UK)
    • a) F. F. Kadlubar in DNA Adducts of Carcinogenic Amines (Eds.: K. Hemminki, A. Dipple, D. E. G. Shuker, F. F. Kadlubar, D. Segerbäck, H. Bartsch), Oxford University Press. Oxford (UK), 1994, pp. 199-216;
    • (1994) Dna Adducts of Carcinogenic Amines , pp. 199-216
    • Kadlubar, F.F.1
  • 29
    • 0242447924 scopus 로고    scopus 로고
    • note
    • 3). Only 3a and 4a were formed (9 % and 5 % yield, respectively).
  • 30
    • 0242531589 scopus 로고    scopus 로고
    • note
    • Compound 4a was quantitatively converted to 3a upon treatment with one equivalent of potassium hydroxide in refluxing toluene.
  • 32
    • 0000126466 scopus 로고
    • Homolytic cleavage of the N-O bond of 4-isoxazolines is well documented. See, for example: a) J. E. Baldwin, R. G. Pudussery, A. K. Qureshi, B. Sklarz, J. Am. Chem. Soc. 1968, 90, 5325-5326; b) A. Padwa, Y. Tomioka, M. K. Venkatramanan, Tetrahedron Lett. 1987, 28, 755-758; c) A. Padwa, M. Meske, Z. Ni, Tetrahedron 1995, 51, 89-106.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 5325-5326
    • Baldwin, J.E.1    Pudussery, R.G.2    Qureshi, A.K.3    Sklarz, B.4
  • 33
    • 0242531587 scopus 로고
    • Homolytic cleavage of the N-O bond of 4-isoxazolines is well documented. See, for example: a) J. E. Baldwin, R. G. Pudussery, A. K. Qureshi, B. Sklarz, J. Am. Chem. Soc. 1968, 90, 5325-5326; b) A. Padwa, Y. Tomioka, M. K. Venkatramanan, Tetrahedron Lett. 1987, 28, 755-758; c) A. Padwa, M. Meske, Z. Ni, Tetrahedron 1995, 51, 89-106.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 755-758
    • Padwa, A.1    Tomioka, Y.2    Venkatramanan, M.K.3
  • 34
    • 0028897127 scopus 로고
    • Homolytic cleavage of the N-O bond of 4-isoxazolines is well documented. See, for example: a) J. E. Baldwin, R. G. Pudussery, A. K. Qureshi, B. Sklarz, J. Am. Chem. Soc. 1968, 90, 5325-5326; b) A. Padwa, Y. Tomioka, M. K. Venkatramanan, Tetrahedron Lett. 1987, 28, 755-758; c) A. Padwa, M. Meske, Z. Ni, Tetrahedron 1995, 51, 89-106.
    • (1995) Tetrahedron , vol.51 , pp. 89-106
    • Padwa, A.1    Meske, M.2    Ni, Z.3
  • 35
    • 0242616242 scopus 로고    scopus 로고
    • note
    • Aziridine 16 f could be isolated by column chromatography when nitrone 1 f and 2 were reacted with triethylamine in excess in toluene at 110°C (24 %). (Equation presented).
  • 37
    • 0242616241 scopus 로고    scopus 로고
    • note
    • Futhermore, no evidence for formation of the dimer of triphenylmethane radical (the Ullman hydrocarbon 18) was found. (Equation presented).
  • 40
    • 0345397362 scopus 로고
    • In 1983, the reaction of 2-morpholin-4-yl-acrylonitrile (2) with nitrone 1b was reported by Döpp to give 1-morpholin-4-yl-3-phenyl-3-phenylaminoethanone 6b as the sole product (34 %); however, its formation remained unexplained: D. Döpp, J. Walter, Heterocycles 1983, 20, 1055-1061.
    • (1983) Heterocycles , vol.20 , pp. 1055-1061
    • Döpp, D.1    Walter, J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.