ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Further evidence is presented that the 2-norbornyl cation is stabilized primarily by C(2)-C(6) bridging, and that C(2)-C(7) bridging leads to prohibitive strain. Thus, a comparison of the heats of hydrogenation of nortricyclene 17 and bicyclo[3. 2. 0. 0.2,7]heptane 18 indicates that the strain energy of the latter is ca. 21.5 kcal/mol higher that that of 17. Furthermore, 6-exo-2-oxabicyclo[2. 2. 1]heptyl sulfonates 8 ionize with strong O(2) participation to the bridged oxonium ion 12. In contrast, 2-endo-7-oxabicyclo[2.2.1]heptyl sulfonates 11 ionize without O(7) participation to form the unbridged carbenium ion 15.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19880710512
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