𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Fragmentation of Homoallylic Alkoxides. Preparation of 1-(3′-cyclopentenyl)-2-alkanones from 2-substituted bicyclo[2.2.1]hept-5-en-2-ols

✍ Scribed by Roger L. Snowden

Publisher
John Wiley and Sons
Year
1983
Tongue
German
Weight
456 KB
Volume
66
Category
Article
ISSN
0018-019X

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The potassium 2‐substituted bicyclo[2.2.1]hept‐5‐en‐2‐alkoxides derived from alcohols 2–9 at 30° in hexamethylphosphoric triamide (HMPA) afford 1‐(3′‐cyclopentenyl)‐2‐alkanones 10–19 via heterolytic C(1), C(2)‐allylic bond cleavage in the substrate alkoxide followed by intramolecular protonation of the resultant transient allylic anion.

📜 SIMILAR VOLUMES

Metathesis polymerization of endo-5- and
Metathesis polymerization of endo-5- and exo-5-chloromethylbicyclo[2.2.1]hept-2-ene and of 5,5-bis(chloromethyl)bicyclo[2.2.1]hept-2-ene; microstructure of the polymers
✍ Kenneth J. Ivin; Luk-Mui Lam; John J. Rooney 📂 Article 📅 1994 🏛 John Wiley and Sons 🌐 English ⚖ 494 KB

## Abstract The three title monomers were polymerized using a variety of Ru‐, Ir‐, Mo‐, W‐ and Re‐based metathesis catalyst systems to yield polymers having a wide range of __cis__ double bond contents in each case. The ^13^C NMR spectra of the polymers were interpreted in terms of __cis/trans__, h