Premium
Copper‐Catalyzed Synthesis of 1,2‐Disubstituted Cyclopentanes from 1,6‐Dienes by Ring‐Closing Kharasch Addition of Carbon Tetrachloride
Author(s) -
MuñozMolina José María,
Belderraín Tomás R.,
Pérez Pedro J.
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800364
Subject(s) - chemistry , cyclopentanes , cyclopentane , catalysis , carbon tetrachloride , copper , stereospecificity , medicinal chemistry , diene , organic chemistry , magnesium , natural rubber
The reaction of carbon tetrachloride (CCl 4 ) with various 1,6‐heptadienes catalyzed by copper homoscorpionate complexes affords cyclization products in moderate to high yields. The process involves the addition of the trichloromethyl radical to the diene followed by a 5‐ exo‐trig cyclization reaction, resulting in the formation of the cis ‐3‐chloromethyl‐4‐(2,2,2‐trichloroethyl)cyclopentane isomers in a highly regiospecific and stereospecific manner. We have studied the use of magnesium (Mg) as reducing agent for the regeneration of copper(I) catalysts. This method has afforded heterocycles in high yields even in the cases of diallyl ether (DAE) and tert ‐butyl N,N ‐diallylcarbamate (TBDAC).