Iodine ate complexes and N-lithiobenzocyclobutenamine intermediates in the reactions of α-lithionitriles with benzyne

✍ Scribed by Sasmita Tripathy; Helmi Hussain; Tony Durst

• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 100 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)01493-3

✦ Synopsis

a-Lithionitriles add to benzynes to give N-lithiobenzocyclobutenamines in a two-step process. The intermediate aryllithiums can be trapped prior to cyclization with iodobenzene or 2,6-dimethoxyiodobenzene to form iodine-ate complex intermediates which fragment preferentially to 2-(a-cyanobenzyl)iodobenzenes. The N-lithiobenzocyclobutenamines undergo ring opening to yield either 2-substituted benzonitriles or a-substituted benzylcyanides depending on the substitution pattern on the aryl and cyclobutene rings.