Thermal stereomutations and vinylcyclopropane-to-cyclopentene rearrangement of 2-methylene-3-spirocyclopropanebicyclo[2.2.1]heptane [9]

Journal of the American Chemical Society

Volumn 121, Issue 47, 1999, Pages 11018-11019

  Baldwin, John E ^a   Shukla, Rajesh ^a  

^a SYRACUSE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTENE DERIVATIVE; CYCLOPROPANE DERIVATIVE; HEPTANE;

ELECTROCHEMISTRY; ENERGY TRANSFER; GEOMETRY; ISOMERISM; LETTER; REACTION ANALYSIS; STEREOCHEMISTRY; THERMODYNAMICS;

EID: 0033486040     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992603k     Document Type: Letter

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23. For perspectives on reaction dynamics in some organic reactions, see: (a) Carpenter, B. K. Acc. Chem. Res. 1992, 25, 520-528. (b) Carpenter, B. K. Am. Sci. 1997, 85, 138-149. Carpenter, B. K. Angew. Chem., Int. Ed. 1998, 37, 3340-3350.
24. For perspectives on reaction dynamics in some organic reactions, see: (a) Carpenter, B. K. Acc. Chem. Res. 1992, 25, 520-528. (b) Carpenter, B. K. Am. Sci. 1997, 85, 138-149. Carpenter, B. K. Angew. Chem., Int. Ed. 1998, 37, 3340-3350.
25. Stereochemical studies on two 1-ethenylbicyclo[4.1.0]heptane to bicyclo[4.3.0]non-1(9)-ene isomerizations have shown that antarafacial utilization of the allylic moiety does occur, even when extended Z-2-ex diradical conformations are not accessible, see: (a) Baldwin, J. E.; Bonacorsi, S. J.; Burrell, R. C. J. Org. Chem. 1998, 63, 4721-4725. (b) Baldwin, J. E.; Burrell, R. C. J. Org. Chem. 1999, 64, 3567-3571.
26. Stereochemical studies on two 1-ethenylbicyclo[4.1.0]heptane to bicyclo[4.3.0]non-1(9)-ene isomerizations have shown that antarafacial utilization of the allylic moiety does occur, even when extended Z-2-ex diradical conformations are not accessible, see: (a) Baldwin, J. E.; Bonacorsi, S. J.; Burrell, R. C. J. Org. Chem. 1998, 63, 4721-4725. (b) Baldwin, J. E.; Burrell, R. C. J. Org. Chem. 1999, 64, 3567-3571.
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29. 2) is not known with much precision, for the rate constants were derived from limited data.
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