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Bridged and unbridged norbornyl cations

✍ Scribed by Cyril A. Grob; Reinhard Hanreich; Adrian Waldner

Book ID: 104234202
Publisher: Elsevier Science
Year: 1981
Tongue: French
Weight: 177 KB
Volume: 22
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)81870-0

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✦ Synopsis

The solvolysis rates and products of 6-substituted 2-norbornyl-p-toluenesulfonates 1, and 5 are controlled by 1,3-bridging, i.e. by the degree of bonding between C(6) and C(2) in the intermediate norbornyl cations.

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The effects of substituents at C5, C6 and C7 on the solvolysis rates of 2-norbornyl p-toluene sulfonates confirm that through space induction is directional and depends on distance and bridging strain.

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Norbornanes. Part 20. Inductivity and bridging in 2-norbornyl cations

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As derived from the Hammetr equation log k/ko = pI 'cr ? where k and ko are rate constants for substituted and unsubstituted tosylates, respectively, and u? are inductive substituent constants [2]. The p , values for C(1) in 3 and 4 are presented and discussed in this communication. The dotted lines

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Further evidence is presented that the 2-norbomyl 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 bicycl0[3.2.0.0~.~]heptane 18 indicates that the strain energy of

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no satisfactory explanation for the complete order of the ozonide anions at room temperature, which is in contrast with the comparable RbN02151. Intermolecular interactions between the ozonide ions (dimerization) can be ruled out on the grounds of the large intermolecular distances[31. Also still in

The Norbornyl Cation: Prototype of a 1,3

The Norbornyl Cation: Prototype of a 1,3-Bridged Carbocation

✍ Prof. Dr. Cyril A. Grob 📂 Article 📅 1982 🏛 John Wiley and Sons 🌐 English ⚖ 928 KB

## Abstract The protracted discussion of whether 2‐norbornyl cations are bridged or unbridged, __i.e.__ nonclassical or classical, has lost most of its meaning, because these terms apply to the extremes of a graded series of structures. This is shown by a study of the solvolysis of stereoisomeric 6

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