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Volumn 68, Issue 17, 2003, Pages 6661-6671

Novel photoreactions of 2-Aza-1,4-dienes in the triplet excited state and via radical-cation intermediates. 2-Aza-di-π-methane rearrangements yielding cyclopropylimines and N-vinylaziridines

Author keywords

[No Author keywords available]

Indexed keywords

OLEFINS; PHOTOCHEMICAL REACTIONS; POSITIVE IONS; SUBSTITUTION REACTIONS;

EID: 0043011023     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034452g     Document Type: Article
Times cited : (19)

References (48)
  • 3
    • 85052767485 scopus 로고
    • Padwa, A., Ed.; Marcel Dekker: New York
    • (b) Zimmerman, H. E. In Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker: New York, 1991; Vol. 11, pp 1-36.
    • (1991) Organic Photochemistry , vol.11 , pp. 1-36
    • Zimmerman, H.E.1
  • 4
    • 0001331918 scopus 로고
    • Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, UK
    • (c) De Lucchi, O.; Adam, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, UK, 1991; Vol. 5, pp 193-214.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 193-214
    • De Lucchi, O.1    Adam, W.2
  • 8
    • 85052773289 scopus 로고
    • Padwa, A., Ed.; Marcel Dekker: New York
    • (d) Demuth, M. In Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker: New York, 1991; Vol. 11, pp 37-109.
    • (1991) Organic Photochemistry , vol.11 , pp. 37-109
    • Demuth, M.1
  • 9
    • 0010490952 scopus 로고
    • Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, UK
    • (e) Demuth, M. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, UK, 1991; Vol. 5, pp 215-237.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 215-237
    • Demuth, M.1
  • 19
    • 0042523087 scopus 로고    scopus 로고
    • note
    • (a) Recent studies carried out by us show that 1-aza-1,4-dienes also undergo SET-sensitized 1-ADPM rearrangements (refs 7b and 7c).
  • 22
    • 0043024091 scopus 로고    scopus 로고
    • note
    • (a) Within this area of SET-promoted di-π-methane rearrangements, we have described recently the first examples of 1-ADPM and DPM rearrangements that take place via radical-anion intermediates (ref 8b).
  • 28
    • 0042523086 scopus 로고    scopus 로고
    • note
    • (a) Previous attempts by Adam et al. (ref 13b) to promote the formation of oxiranes by the DPM rearrangement were unsuccessful.
  • 31
    • 0043024092 scopus 로고    scopus 로고
    • note
    • 2 was used as solvent. However, when the reaction was repeated in t-BuOH the cyclopropylimine 11b was isolated in low yield.
  • 35
    • 0041521269 scopus 로고    scopus 로고
    • note
    • At this point it is not possible to establish the structure of the minor product based on spectroscopic evidence. Our aim is to obtain a crystalline sample that would permit us to determine its structure by X-ray diffraction analysis.
  • 36
    • 0043024090 scopus 로고    scopus 로고
    • note
    • 2 (SHELXTL version 5.1). The non-hydrogen atoms were refined anisotropically. The hydrogen atoms were included in calculated positions, R1 = 0.047 for 1429 observed reflections and wR2 = 0.134 (all data). Further crystallographic details for the structure reported in this paper may be obtained from the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge CB2 1EZ, U.K.; depository no. CCDC-198688.
  • 37
    • 0001373505 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK
    • For reviews see: (a) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK, 1991; Vol. 5, pp 899-970.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 899-970
    • Hudlicky, T.1    Reed, J.W.2
  • 44
    • 0042523083 scopus 로고    scopus 로고
    • note
    • 1H NMR analysis of the photomixture indicates the presence of two cyclopropane derivatives. However, all the attempts to isolate them resulted in decomposition of the photoproducts. No N-vinylaziridine was detected in this instance.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.