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

Abstract

GRAPHICAL ABSTRACT

Keywords:

• Bicyclic alkenes
• catalysis
• 7-oxanorbornadienes
• ring-opening reactions
• ruthenium

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.