Synthesis of cis,cis,cis,cis-[5.5.5.4]-1-Azafenestrane with Discovery of an Unexpected Dyotropic Rearrangement

✍ Scribed by Scott E. Denmark; Justin I. Montgomery

• Publisher: John Wiley and Sons
• Year: 2005
• Tongue: English
• Weight: 336 KB
• Volume: 44
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.200500367

✦ Synopsis

Fenestranes [1] [fenestra (Lat.), window] are a unique family of compounds with four fused carbocycles that share a central quaternary carbon atom which exhibits planarizing distortion (for example, 1, Scheme 1). [2] By changing ring sizes and ringfusion configurations, variable planarization of the central carbon atom results, thus giving chemists a tool with which to probe one of the cornerstone theories of organic chemistry. [3] Unfortunately, unsubstituted fenestranes are low-molecularweight hydrocarbons, and therefore crystallization for singlecrystal analysis and quantification of the distortions to the central carbon atom is difficult. [4] By substituting a nitrogen Scheme 1. cis,cis,cis,cis-[5.5.5.5]-Fenestrane (1) and cis,cis,cis,cis-[5.5.5.5]-1-azafenestrane•BH 3 (2).