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Volumn 119, Issue 24, 1997, Pages 5682-5689

Hydrogen migration vs carbon migration in dialkylcarbenes. A study of the preferred product in the carbene rearrangements of ethylmethylcarbene, cyclobutylidene, 2-norbornylidene, and 2-bicyclo[2.1.1]hexylidene

Author keywords

[No Author keywords available]

Indexed keywords

CARBENOID; CARBON; HYDROGEN; ORGANIC COMPOUND; UNCLASSIFIED DRUG;

EID: 0030818024     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970181d     Document Type: Article
Times cited : (99)

References (65)
  • 6
    • 0004076101 scopus 로고
    • Ronald Press: New York, NY
    • Hine, J. Divalent Carbon; Ronald Press: New York, NY, 1964.
    • (1964) Divalent Carbon
    • Hine, J.1
  • 11
    • 0342464167 scopus 로고
    • Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, NY
    • Moss, R. A. In Carbenes; Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, NY, 1973; Vol. I, p 153.
    • (1973) Carbenes , vol.1 , pp. 153
    • Moss, R.A.1
  • 12
  • 33
    • 0002216732 scopus 로고
    • and references therein
    • Nickon, A. Acc. Chem. Res. 1993, 26, 84 and references therein.
    • (1993) Acc. Chem. Res. , vol.26 , pp. 84
    • Nickon, A.1
  • 53
    • 1842269712 scopus 로고    scopus 로고
    • Storer and Houk (ref 21) find that tunneling effects might further lower the barrier and improve the agreement between experiment and theory
    • Storer and Houk (ref 21) find that tunneling effects might further lower the barrier and improve the agreement between experiment and theory.
  • 57
    • 0004234620 scopus 로고    scopus 로고
    • Brinker, U. Ed.; JAI Press: New York in press
    • For a recent review, see: Platz, M. S. Advances in Carbene Chemistry II; Brinker, U. Ed.; JAI Press: New York in press.
    • Advances in Carbene Chemistry II
    • Platz, M.S.1
  • 59
    • 1842391161 scopus 로고    scopus 로고
    • note
    • 12, suggesting that τ is controlled by unimolecular rearrangements in these solvents. An oxadiazoline precursor was employed. Photolysis of this precursor generated 2 as a species trappable with either pyridine or tetramethylene (TME). It was found that [TME] cannot completely suppress the formation of methylenecyclopropane and cyclobutane and changes the ratio on which these two products are formed. Again the involvement of nitrogenous excited states in product formation is indicated.
  • 64
    • 1842392141 scopus 로고    scopus 로고
    • A much more detailed discussion based on the molecular orbitals can be found in Schoeller's work (ref 64)
    • A much more detailed discussion based on the molecular orbitals can be found in Schoeller's work (ref 64).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.