Selectivity as a mechanistic tool in solvolytic reactions.

✍ Scribed by Addy Pross

• Publisher: Elsevier Science
• Year: 1975
• Tongue: French
• Weight: 158 KB
• Volume: 16
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)71941-1

✦ Synopsis

Harris has recently reported that in the solvolysis of adamantyl arenesulphonates, water molecules exhibit greater nucleophiltcity than those of ethanol (kethanol kwater <I) in an aqueous solut ion1 . This inversion in the relative nucleophilic behaviour was attributed to the abilityofwater to form a double hydrogen bond in the solvent separated ion oxygen atoms of the arenesulphonate leaving group (I). This, in contrast to form such a structure (II).