Sulfur participation in solvolysis involving four-membered ring intermediates

✍ Scribed by Ernest L. Eliel; William H. Pearson; Linda M. Jewell; Anthony G. Abatjoglou; William R. Kenan Jr.

• Book ID: 104237200
• Publisher: Elsevier Science
• Year: 1980
• Tongue: French
• Weight: 266 KB
• Volume: 21
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)85465-4

✦ Synopsis

swronary-Neighboring group participation via four-membered ring intermediates resulting in complete rearrangement occurs in the methanoiysis of ~~CkXIi2C6H5)CH2Cii(~)OTS when ~=~=~=I& and when R=R_=M~, R-H. No rearrangement is found for R.=R_=R_=H or R.=L=li, R_=Ms. The I L 3 case of Rl :Ms: B2=R3iH is intermediate. Cases of neighboring group participation by sulfur involving four-membered rings are extremely rare. 1,2 Paquette, Meehan and Wise3 have observed rate enhancement by nearly four orders of magnitude in solvolysis of a tosylate in a caged system where a sulfur atom was