On the relationship between structure and reaction rate in olefin ring-closing metathesis.
In the RCM reactions of a series of simple α,ω-dienes, the relative order of reactivity has been unambiguously determined showing that cyclohexene forms faster than cyclopentene or cycloheptene. 1,5-Hexadiene inhibits the RCM of 1,7-octadiene; 1,5-hexadiene cannot progress to the RCM product (cyclobutene) but forms an unexpectedly stable cyclic η(2)-complex.
Ashworth
Ian W
IW
AstraZeneca Global Research and Development, Silk Road Business Park, Charter Way, Macclesfield, SK10 2NA, UK.
Carboni
Davide
D
Hillier
Ian H
IH
Nelson
David J
DJ
Percy
Jonathan M
JM
Rinaudo
Giuseppe
G
Vincent
Mark A
MA
D000475:Alkenes / Q000737:chemistry*; D003500:Cyclization; D053138:Cyclohexenes / Q000737:chemistry; D003517:Cyclopentanes / Q000737:chemistry; D007700:Kinetics; D015394:Molecular Structure
D000475:Alkenes; D053138:Cyclohexenes; D003517:Cyclopentanes; C052568:cyclohexene