✦ LIBER ✦

Synthesis and electrophilic reactions of a conformationally rigid cyclopropylcarbinyl cation. An unusual synthesis of substituted benz[a]azulenes.

✍ Scribed by Mark E. Jason

Book ID: 104220676
Publisher: Elsevier Science
Year: 1982
Tongue: French
Weight: 204 KB
Volume: 23
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)87177-4

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✦ Synopsis

A tropylium-substituted cyclopropane has been prepared which is rigidly held in the "bisected" conformation. Its electrophilic reactions are also investigated.

Bond length asymmetry in cyclopropanes, as induced by aromatic substituents, has recently been an object of attention in our 1aboratories.l We have observed shortening of the cyclopropane bonds opposite gem-diphenyl or 2,2'-biphenyl substitution, as in structures 1 and 2, re-" spectively.lb The asymmetry in 2 has been explained in terms of cyclopropane-to-biphenyl charge transfer in analogy with the stabilization of cyclopropylcarbinyl cations. The orbital interaction, using Walsh orbitals on cyclopropane, is seen in 3.2s3

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