Solvolytic hydroperoxide rearrangements IV. Selective rearrangement of spiro[5,2]octan-4-ol.

✍ Scribed by Robert C. Ronald; Suzanne M. Ruder; Thomas S. Lillie

• Book ID: 104227343
• Publisher: Elsevier Science
• Year: 1987
• Tongue: French
• Weight: 276 KB
• Volume: 28
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)95667-3

✦ Synopsis

Rearrangement of spiro octan-4-01, 1, in acidified THF-H202 is a selective process in which substitution occurs with retention of configuration and ring-expansion with inversion of the carbinyl center.

Recently, we reported that rearrangements of certain cyclopropyl carbinols in acidified 90% H202-THF occur stereoselectively to afford ring-expansion products with defined