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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 8
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Original Articles

Ruthenium-Catalyzed Nucleophilic Ring-Opening Reactions of 7-Oxabenzonorbornadienes with Methanol

, , &
Pages 1181-1187 | Received 01 Sep 2011, Published online: 21 Feb 2013
 

Abstract

GRAPHICAL ABSTRACT

ACKNOWLEDGMENTS

This work was supported by Merck Frosst Centre for Therapeutic Research and Natural Sciences and Engineering Research Council of Canada (NSERC). K. J. thanks NSERC for a postgraduate scholarship (CGS M). Karine Villeneuve and Avila De Sousa are thanked for preliminary experiments.

Notes

a Isolated yield after column chromatography.

b 20 equivalent of MeOH was used.

c 7-Oxabenzonorbornadiene 1a was recovered (22–91%).

d The reaction mixture was stirred for 4 h.

e The reaction mixture was stirred for 6 h.

a Isolated yield after column chromatography.

b Yields in brackets are the amount of the corresponding naphthol isomerization product isolated.

c Some 7-oxabenzonorbornadiene was recovered.

d The reaction was run at 80 °C.

e Decomposition of 7-oxabenzonorbornadiene 1i was observed.

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