104525-51-1Relevant articles and documents
The Reaction of 9-(2',3'-Dideoxy-β-D-glycero-pent-2-Enofuranosyl)-adenine Derivatives with Arene- and Alkenesulfenyl Chlorides. An Unusual Ring Opening Reaction of Thiiranium Ions
Welch, C. J.,Bazin, H.,Chattopadhyaya, J.
, p. 343 - 357 (2007/10/02)
A series of arenesulfenyl chlorides and methanesulfenyl chloride were reacted in pyridine solution with 6-N-dibenzoyl-9-(2',3'-dideoxy-β-D-glycero-pent-2-enofuranosyl)adenine (1b).In each case, the relative abundance of isomeric β-chloroarene/alkene sulfides was estimated and used to assess the relative thermodynamic stabilities of the lyxo and ribo thiiranium ion intermediates and their steric susceptibilities to attack by nucleophile (Cl-).Subsequently, the β-chloroarene/alkene sulfides 8a-d to 13 a-d, upon alkaline treatment, underwent an unprecedented ylide-mediated β elimination of the intermediary lyxo and ribo thiiranium ions, to give only 2'-ene-thiol ethers 14-19.