Norbornanes . Part 21. Bridging strain in norbornyl and oxanorbornyl cations | Zendy

Flury Peter | Zendy; Grob Cyril A. | Zendy; Wang Guang Yi | Zendy; Lennartz HansWerner | Zendy; Roth Wolfgang R. | Zendy

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Norbornanes . Part 21. Bridging strain in norbornyl and oxanorbornyl cations

Author(s) -

Flury Peter,

Grob Cyril A.,

Wang Guang Yi,

Lennartz HansWerner,

Roth Wolfgang R.

Publication year - 1988

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19880710512

Subject(s) - chemistry , 2 norbornyl cation , oxonium ion , ion , heptane , bicyclic molecule , strain (injury) , bridging (networking) , medicinal chemistry , ionization , stereochemistry , standard enthalpy of formation , computational chemistry , organic chemistry , medicine , computer network , computer science

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 .

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