Journal of Organic Chemistry p. 5270 - 5276 (1982)
Update date:2022-08-02
Topics:
Watson, William David
The neat chlorination of 4-chloroanisole produces 1,3,4,5,6-pentachloro-4-methoxycyclohexene in 35percent yield.Mono- and dichlorinated anisoles and a variety of simple substituted anisoles were chlorinated to determine the generality of nonaromatic product formation. 3,4-Dichloroanisole, 4-fluoroanisole, 4-bromoanisole, 4-methylanisole, and 4-chlorophenetole form similar products based on their spectral properties.These products are proposed to form by a cis-1,2-chlorine addition followed by rapid cis-1,4 chlorine addition.On the basis of the NMR data, a predominate configuration is proposed.
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(1983)
