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Volumn , Issue 13, 2001, Pages 2463-2475

A laser flash photolysis study on 2-azido-N,N-diethylbenzylamine - The reactivity of iminoquinone methides in solution

Author keywords

Cycloadditions; Iminoquinone methides; Laser spectroscopy; Nitrenes; Quinoid compounds

Indexed keywords

2 AZIDO N,N DIETHYLBENZYLAMINE; IMINOQUINONE METHIDE DERIVATIVE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0034963927     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200107)2001:13<2463::AID-EJOC2463>3.0.CO;2-6     Document Type: Article
Times cited : (13)

References (65)
  • 3
    • 0033549497 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 1999, 38, 1928-1931.
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 1928-1931
  • 25
    • 0002303355 scopus 로고    scopus 로고
    • Triterpenoid Quinonemethides and Related Compounds (Celastroloids)
    • (Eds.: W. Herz, G. W. Kirby, R. E. Moore, W. Steglich, Ch. Tamm), Springer, Vienna, New York, chapter 1
    • A. A. L. Gunatilaka, Triterpenoid Quinonemethides and Related Compounds (Celastroloids), in: Progress in the Chemistry of Organic Natural Products (Eds.: W. Herz, G. W. Kirby, R. E. Moore, W. Steglich, Ch. Tamm), Springer, Vienna, New York, 1996, vol. 67, chapter 1, p. 1-123.
    • (1996) Progress in the Chemistry of Organic Natural Products , vol.67 , pp. 1-123
    • Gunatilaka, A.A.L.1
  • 29
    • 0004731006 scopus 로고    scopus 로고
    • note
    • A number of possible products with m = 150 were synthesized, among them 2-amino-N-ethylbenzylamine, 2-(ethylamino)-benzylamine, and N-ethyl-N-methyl-o-phenylenediamine. None of the compounds was identical to the product formed in the photolyses.
  • 35
    • 0004730295 scopus 로고
    • Zh. Obshch. Khim. 1990, 60, 469-471.
    • (1990) Zh. Obshch. Khim. , vol.60 , pp. 469-471
  • 42
    • 0004723876 scopus 로고    scopus 로고
    • note
    • 4] (100%). The base peak with m/z = 147 corresponds to the 2-amino-N-ethylbenzonitrilium cation. The very low yield of 11 may be due to hydrolysis of this rather labile compound, yielding 2-aminobenzaldehyde (6). Several attempts were made to synthesize 11 independently. While it was possible to obtain an aminal from 2-nitrobenzaldehyde by refluxing the aldehyde in neat diethylamine for 48 h, all attempts to reduce this compound to 11 failed. Under all conditions tried (catalytic hydrogenation, various catalysts and solvents, presence of diethylamine), the aminal functionality was reduced before the nitro group. 2-Aminobenzaldehyde (6), on the other hand, did not react with diethylamine, polymerizing instead.
  • 44
    • 0004723877 scopus 로고    scopus 로고
    • note
    • -1 is consistent with a assignment of the slow component to didehydroazepine 5.
  • 52
    • 0002120722 scopus 로고
    • Photochemistry of Phenyl Azide
    • (Eds.: D. H. Volman, G. Hammond, D. C. Neckers), John Wiley & Sons Inc.
    • G. B. Schuster, M. S. Platz, Photochemistry of Phenyl Azide, in: Advances in Photochemistry (Eds.: D. H. Volman, G. Hammond, D. C. Neckers), John Wiley & Sons Inc., 1992, vol. 17, p. 69-143.
    • (1992) Advances in Photochemistry , vol.17 , pp. 69-143
    • Schuster, G.B.1    Platz, M.S.2
  • 53
    • 84985143899 scopus 로고
    • Heinzelmann has reported on the formation of simple iminoquinone methides by acid-induced tautomerization of 2-aminobenzaldimines. In the light of the results presented in this study, this assignment has to be incorrect. Most probably, the compounds wrongly identified as neutral iminoquinone methides in fact are the conjugate acids of the iminoquinone methides, which are the 2-aminobenzaldiminium cations; W. Heinzelmann, Helv. Chim. Acta 1978, 61, 618-625.
    • (1978) Helv. Chim. Acta , vol.61 , pp. 618-625
    • Heinzelmann, W.1
  • 64
    • 0004725048 scopus 로고    scopus 로고
    • Schrödinger, Inc., Portland
    • Titan Vers. 1.0.1, Schrödinger, Inc., Portland, 1999.
    • (1999) Titan Vers. 1.0.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.