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A new route to 2,4-dibenzyltetrahydroquinoline. Reversibility of the homolytic aromatic benzylation.

✍ Scribed by O. Porta; G. Sesana

Publisher
Elsevier Science
Year
1978
Tongue
French
Weight
195 KB
Volume
19
Category
Article
ISSN
0040-4039

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✦ Synopsis

The benzyl radical addition to ethylene is a reversible process at 9OOC'. Considering that the addition of a free radical to benzene has been estimated2 to be less exothermic of ca. 11 Kcal/mole than the corresponding addition of a benzyl radical to ethylene, the addition of a benzyl radical to an aromatic ring should be reversible. In fact the homolytic benzylation is pratically unknown in benzene series but, because of the nucleophilic character of the benzyl radical, it is a well known type of reaction with protonated heteroaromatic bases'.

In this communication we report an unusual synthesis of 2,4-dibenzyltetrahydroquinoline from the benzyl radical addition to quinoline and preliminary evidences that this addition also is a reversible process.

πŸ“œ SIMILAR VOLUMES

A novel route to 1-benzyl-1,2,4-triazole
A novel route to 1-benzyl-1,2,4-triazole derivatives through disproportionation of isothiosemicarbazones
✍ Chiji Yamazaki; Mariko Ohno πŸ“‚ Article πŸ“… 1997 πŸ› Journal of Heterocyclic Chemistry 🌐 English βš– 320 KB

## Abstract Aromatic isothiosemicarbazones 1–4 underwent disproportionation at elevated temperature in the presence of a thiol or a thiol‐releasing substance to give 1‐arylmethylene‐3‐alkylthio‐5‐aryl‐1__H__‐1,2,4‐triazole derivatives 6–9 in moderate yields. An isothiosemicarbazone of aliphatic ald