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Rearrangements of azidoquinones. V. Stereoselective acid-catalyzed rearrangements of azidoquinones to .gamma.-cyanoalkylidine- (cyanoarylidine-) .DELTA..alpha.,.beta.-butenolides

✍ Scribed by Moore, Harold Wesley.; Shelden, H. Raymond.; Deters, Donald W.; Wikholm, Ronald J.

Book ID: 111980114
Publisher: American Chemical Society
Year: 1970
Tongue: English
Weight: 898 KB
Volume: 92
Category: Article
ISSN: 0002-7863
DOI: 10.1021/ja00709a043

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Rearrangements of azidoquinones II. Ster

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

✍ Harold W. Moore; H. Raymond Shelden 📂 Article 📅 1968 🏛 Elsevier Science 🌐 French ⚖ 194 KB

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