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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Stereochemical Correspondence among Chemically Disparate Systems: Spirocyclic Phosphoranes, Diarylmethanes, and
D Gust1, P Finocchiaro, K Mislow
1Department of Chemistry, Princeton University, Princeton, New Jersey 08540.
Abstract:
Certain chemical systems which differ greatly in many of their chemical properties may nevertheless exhibit stereochemically isomorphic behavior, i.e., they may be stereochemically correspondent. Two such systems are spirocyclic pentacoordinate molecules and molecules of the type Ar(2)ZX. The consequences of stereochemical correspondence between these two systems are explored in depth.
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Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.