Rearrangements of azidoquinones II. Stereoselective acid-catalyzed rearrangement of azidoquinones to γ-alkylidene (arylidene) -Δga,gb-butenolides

✍ Scribed by Harold W. Moore; H. Raymond Shelden

• Book ID: 104222985
• Publisher: Elsevier Science
• Year: 1968
• Tongue: French
• Weight: 194 KB
• Volume: 9
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)89796-8

✦ Synopsis

Azidoquinones undergo a stereoselective rearrangement in acidic media to give high yields of ring-contracted Y -alkylidene-(or arylidene) -Aa' '-butenolides. This rearrangement is of mechanistic significance in regards to certain reactions which have appeared in the literature, 1,293 and also finds synthetic utility in the preparation of pulvinic acid (41, a naturally occurring Y-arylidene-A o,B butenolide found in a variety of lichens. 4