Cyclic vs. acyclic allylic hydrogen abstraction: An entropy motivated process?

Tetrahedron

Volumn 54, Issue 20, 1998, Pages 5417-5422

  Rothenberg, Gadi ^a   Sasson, Yoel ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; HYDROGEN;

ARTICLE; ENTHALPY; ENTROPY; GEOMETRY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0032516292     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00215-4     Document Type: Article

References (29)

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3. 3. Bridgehead allylic positions are the exception to this rule. See Busfield, W. K.; Grice, I. D.; Jenkins, I. D., Aust. J. Chem., 1991, 44, 1407-1415.
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16. 16. Values were calculated per active hydrogen atom. In the cyclic molecules it was assumed that both allylic hydrogens have equal reactivity, although preferential HA from the pseudo-axial positions of six-membered rings has been suggested. See, for example, Beckwith, A. L. J.; Phillipou, G., Aust. J. Chem., 1976, 29, 1277-1294; Cross, B.; Whitham, G. H., J. Chem. Soc., 1961, 1650-1654.
17. 16. Values were calculated per active hydrogen atom. In the cyclic molecules it was assumed that both allylic hydrogens have equal reactivity, although preferential HA from the pseudo-axial positions of six-membered rings has been suggested. See, for example, Beckwith, A. L. J.; Phillipou, G., Aust. J. Chem., 1976, 29, 1277-1294; Cross, B.; Whitham, G. H., J. Chem. Soc., 1961, 1650-1654.
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22. 28
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25. 24. It should be noted, however, that our computations pertain to the gas phase, while Kwart's experiments were performed in solution.
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