Synthesis of spirodienones by electrophilic intramolecular ipso-cyclization of N-(2-alkynyl)-N-(4-methoxyphenyl)amides

ORGN 18

Xiaoxia Zhang and Richard C. Larock. Department of Chemistry, Iowa State University, Ames, IA 50011
The reaction of N-(2-alkynyl)-N-(4-methoxyphenyl)triflamides or acetamides with ICl at –78 oC affords substituted spirodienones. The steric and electron effect of the substrates on the triple bond of the alkynyl amides has been studied. Aryl-, vinylic-, sily-, and alkyl-substituted acetylenes undergo this cyclization to produce iodo-substituted spiro compounds in excellent yields.
 

New Reactions and Methodology
8:00 AM-12:00 PM, Sunday, March 28, 2004 Anaheim Convention Center -- 303A, Oral

Division of Organic Chemistry

The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004