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Solvolytic studies of stereoisomeric tricyclo[4.2.0.02,4]octan-5-yl derivatives. Conformationally distinguishable cycloprophylcarbinyl cations and the reactivity consequences of differing orbital alignments

✍ Scribed by Leo A. Paquette; O. Cox; M. Oku; R.P. Henzel; J.A. Schwartz


Book ID
104238233
Publisher
Elsevier Science
Year
1973
Tongue
French
Weight
245 KB
Volume
14
Category
Article
ISSN
0040-4039

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✦ Synopsis


The accelerated solvolytic behavior of exo-and endo-bicyclo[3.l.O]alk-2-yl derivatives provides convincing evidence that comparable cyclopropyl participation accompanies ionization of both epimers. 2 The pair of isomers react at very similar rates (k,ndo/k+xo = 1.3-l.5 depending on the leaving group), the small discrepancy arising from ground state energy differ-