The Journal of Organic Chemistry

Regioselectivity of alkoxyisobenzofuran-aryne cycloadditions

DJ Pollart, B Rickborn

Index: Pollart, Daniel J.; Rickborn, Bruce Journal of Organic Chemistry, 1987 , vol. 52, # 5 p. 792 - 798

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Citation Number: 21

Abstract

The cycloaddition reactions of some unsymmetrical arynes with l-ethoxy-3-(trimethylsilyl) isobenzofuran and a naphtho [1, 2-c] furan analogue were examined for prospective regioselectivity. The arynes, generated by lithium tetramethylpiperidide induced dehydrohalogenation of the appropriate haloaromatics, were 3-bromo-, 3-chloro-, 3-methoxy- , and 3-methylbenzyne, 3, 4-pyridyne, and 1, 2-naphthalyne. Regioselectivities ranged ...