✦ LIBER ✦
Regioselectivity of fluoride ion-induced intramolecular nucleophilic cyclization of heptafluoronaphthyl sulfur diimides 2NfFNSNSiMe3 and 2NfFSNSNS1Me3
✍ Scribed by Irina Yu. Bagryanskaya; Yuri V. Gatilov; Alexey O. Miller; Makhmut M. Shakirov; Andrey V. Zibarev
- Publisher
- John Wiley and Sons
- Year
- 1994
- Tongue
- English
- Weight
- 373 KB
- Volume
- 5
- Category
- Article
- ISSN
- 1042-7163
No coin nor oath required. For personal study only.
✦ Synopsis
Abstract
The title reaction is highly regioselective, leading in both cases to 4,5,6,7,8,9‐hexafluoronaphtho[1,2‐c]‐[1,2,5]thiadiazole (whose struture is confirmed by X‐ray structure analysis) and 4,5,6,7,8,9‐hexafluoronaphtho[2,3‐c][1,2,5]thiadiazole in ∼94 : 6 ratio. The preferred direction of cyclization is consistent with final product thermodynamics as well as factors of kinetic control for orbital‐controlled reactions (calculated by use of frontier MOs theory).