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Volumn 58, Issue 34, 2002, Pages 6943-6950

The kinetics, stereochemistry, and deuterium isotope effects in the α-pinene pyrolysis. Evidence for incursion of multiple conformations of a diradical

Author keywords

1,3 sigmatropic shift; Alloocimine; Dipentene; Pinene; Pyrolysis

Indexed keywords

6 TRIDEUTERIOMETHYL ALPHA PINENE; ALLOOCIMINE; ALPHA PYRONENE; DEUTERIUM; IMINE; ISOTOPE; LIMONENE; PINENE; PYRONE DERIVATIVE; RADICAL; UNCLASSIFIED DRUG;

EID: 0037136381     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00676-2     Document Type: Article
Times cited : (26)

References (20)
  • 1
    • 33947342908 scopus 로고
    • By hydrogenation, dipentene product was postulated to be responsible for the thermally induced loss of optical activity of α-pinene. Subsequent work established that, in addition, α-pinene undergoes racemization albeit slower than formation of dipentene
    • (a) Conant J.B., Carlson G.H. J. Am. Chem. Soc. 51:1927;3464. By hydrogenation, dipentene product was postulated to be responsible for the thermally induced loss of optical activity of α-pinene. Subsequent work established that, in addition, α-pinene undergoes racemization albeit slower than formation of dipentene
    • (1927) J. Am. Chem. Soc. , vol.51 , pp. 3464
    • Conant, J.B.1    Carlson, G.H.2
  • 8
    • 0004266297 scopus 로고
    • Hydrocarbon thermal isomerizations
    • A.P. Marchand, & R.E. Lehr. New York: Academic Chapter 1
    • Gajewski J.J. Hydrocarbon thermal isomerizations. Marchand A.P., Lehr R.E., Pericyclic Reactions. Vol. 1:1980;Academic, New York. Chapter 1.
    • (1980) Pericyclic Reactions , vol.1
    • Gajewski, J.J.1
  • 9
    • 0000813312 scopus 로고
    • In a perhaps more relevant example, the stereochemistry of the vinylcyclobutane rearrangement shows little preference for orbital symmetry control in a system where methyls are stereolabels on the migrating carbon and the migration terminus
    • Baldwin J.E., Villarica K.A., Freedberg D.I., Anet F.A.L. J. Am. Chem. Soc. 116:1994;10845. In a perhaps more relevant example, the stereochemistry of the vinylcyclobutane rearrangement shows little preference for orbital symmetry control in a system where methyls are stereolabels on the migrating carbon and the migration terminus: Baldwin J.E., Burrell J.E. J. Org. Chem. 67:2002;3249.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 10845
    • Baldwin, J.E.1    Villarica, K.A.2    Freedberg, D.I.3    Anet, F.A.L.4
  • 10
    • 0037123650 scopus 로고    scopus 로고
    • Baldwin J.E., Villarica K.A., Freedberg D.I., Anet F.A.L. J. Am. Chem. Soc. 116:1994;10845. In a perhaps more relevant example, the stereochemistry of the vinylcyclobutane rearrangement shows little preference for orbital symmetry control in a system where methyls are stereolabels on the migrating carbon and the migration terminus: Baldwin J.E., Burrell J.E. J. Org. Chem. 67:2002;3249.
    • (2002) J. Org. Chem. , vol.67 , pp. 3249
    • Baldwin, J.E.1    Burrell, J.E.2
  • 16
    • 0011249491 scopus 로고    scopus 로고
    • These values are altered slightly from those reported in Ref. 2 due to better data reduction techniques
    • These values are altered slightly from those reported in Ref. 2 due to better data reduction techniques.
  • 17
    • 0011224702 scopus 로고    scopus 로고
    • This value was reported in Ref. 2 to be more than 9:1 based on peak heights. Subsequent studies suggest the smaller value of 5 but with substantial error - see Section 4
    • This value was reported in Ref. 2 to be more than 9:1 based on peak heights. Subsequent studies suggest the smaller value of 5 but with substantial error - see Section 4.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.