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Volumn 73, Issue 15, 2008, Pages 5926-5932

C-H carbene insertion of α-diazo acetamides by photolysis in non-conventional media

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; CHEMICAL REACTIONS; HEXANE; MERCURY (METAL); WATER VAPOR;

EID: 48249150763     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800980c     Document Type: Article
Times cited : (33)

References (51)
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    • (2005) Chem. Rev , vol.105 , pp. 3095-3165
    • Li, C.J.1
  • 30
    • 0000677232 scopus 로고
    • Li, C. J. Chem. Rev. 1993, 93, 2023-2035.
    • (1993) Chem. Rev , vol.93 , pp. 2023-2035
    • Li, C.J.1
  • 31
    • 48249102550 scopus 로고    scopus 로고
    • Lubineau, A.; Auge, J. Top. Curr. Chem. 1999206.
    • Lubineau, A.; Auge, J. Top. Curr. Chem. 1999206.
  • 42
    • 48249147252 scopus 로고    scopus 로고
    • Considering continuing assumption by the organic chemistry community on the reactivity of diazo substrates via singlet or triplet carbene species, it could be supposed for this case that it may occur via singlet carbene. 47-49 In line with this assumption, we performed DFT calculations assuming singlet carbene (derived from 16a) as the reactive species, and the observed modeling reaction pathways were consistent with the experimental 16b/16c ratio Table 4, However, due to recent studies by femtosecond flash photolysis which imply the formation of excited diazo species on the Wolff rearrangement50 and 1,2-H shift,51 another open possibility is that the C-H insertion may occur instead via excited diazo species
    • 51 another open possibility is that the C-H insertion may occur instead via excited diazo species.
  • 49
    • 0001741580 scopus 로고    scopus 로고
    • Gutsche, C. D.; Bachman, G. L.; Udell, W.; Bauerlei.S, J. Am. Chem. Soc. 1971, 93, 5172-5180.
    • Gutsche, C. D.; Bachman, G. L.; Udell, W.; Bauerlei.S, J. Am. Chem. Soc. 1971, 93, 5172-5180.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.