The nucleophilic efficiency of remote cyclopropane in intramolecular displacement reactions: synthesis and acetolysis of 2-(trans-3-bicyclo[3.1.0]) Ethyl p-nitrobenzenesulfonate

✍ Scribed by G.Dann Sargent; Robert L. Taylor; Wolfgang H. Demisch

• Publisher: Elsevier Science
• Year: 1968
• Tongue: French
• Weight: 290 KB
• Volume: 9
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)89736-1

✦ Synopsis

Over the past two decades, increasing attention has been devoted to the nucleophilicity of carbon-carbon bonding electrons. Essentially four types of nucleophile within this class have emerged: aromatic pi electrons, (l-3) carbon-carbon double bonds, (1.2,h) cyclopropane carbon-carbon 8igm bonds, (1,2,5-8) and other carbon-carbon eigma bonds. (1,2,9) In the transition state for nucleophilic displacement, the first two types of nucleophile in this list