✦ LIBER ✦
Substitution of 9-(α-bromo-α-arylmethylene)fluorenes by thiolate ions in aqueous acetonitrile
✍ Scribed by Zvi Rappoport; Bagrat A. Shainyan
- Publisher
- John Wiley and Sons
- Year
- 1997
- Tongue
- English
- Weight
- 98 KB
- Volume
- 10
- Category
- Article
- ISSN
- 0894-3230
No coin nor oath required. For personal study only.
✦ Synopsis
The substitution of 9-(␣-bromo-␣-arylmethylene)fluorenes by MeS ؊ and p-TolS ؊ ions in 80% MeCN-20% H 2 O is a second-order reaction. With MeS ؊ , for the change of the ␣-aryl group, Hammett's = 1•07 in MeCN. The reaction rate decreases on increasing the water content of the medium. The reactions proceed by the Ad N -E route and no competitive S N 1 reaction was observed. The expected influence of the changes in the substituent, solvent, nucleophile and nucleofuge on the competition between the Ad N -E and S N 1 reactions was analyzed.