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(4+2)-cycloadditions of substituted arenediazocyanides: A kinetic study of a new dienophile

✍ Scribed by Duane P. Gapinski; Michael F. Ahern

Book ID
104221173
Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
242 KB
Volume
23
Category
Article
ISSN
0040-4039

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✦ Synopsis

the rate constants of the (4+2)-cycloaddltlon reaction between substjtuted E-arenediazocyanides and 2,3-dimethyl-1,3-butadlene have been determined in several solvents The reaction displays linear Hammett behavior, the data suggest a concerted reaction mechanism Since the initial use of azoesters by Diels and Alder,' many different types of azo compounds have been successfully used as (4+2)-cycloaddltlon reaction partners 2 However, this general reactivity toward ConJugated dlenes has not been realized for aromatic azo dlenophlles 3 We have recently reported the successful utilization of E-arenedlazocyanldes 2 as cycloaddltlon reaction partners with a wide variety of dlenes to form novel reduced pyndazine ring systems J_ 4 We further observed that the arenedlazocyanldes, when reacted with unsymmetrical dlenes, exhibited a variable degree of regioselectivity, depending upon the particular

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