Single and Double Stereoselective Ring Expansion of 1,2,3,4-Tetrahydro-1,4-naphthalenedimethanol Ditosylates

✍ Scribed by Dumitriu, Angela ;Elian, Mihai ;Clorânescu, Ecaterin

• Book ID: 102786282
• Publisher: Wiley (John Wiley & Sons)
• Year: 1982
• Tongue: English
• Weight: 522 KB
• Volume: 115
• Category: Article
• ISSN: 0009-2940
• DOI: 10.1002/cber.19821150129

✦ Synopsis

Abstract

The formolysis of cis‐ and trans‐ditosylates 7a and 7b yielded the mixed esters 13 (at 55°C) or the diols 11 (at 100°C, after LAH reduction) by single and double ring expansion, respectively. The reactions are stereoselective, occurring with retention of configuration, which points to the intermediacy of phenonium ions.