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Synthesis 2012; 44(17): 2713-2722
DOI: 10.1055/s-0032-1316686
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of C1-Substituted Oxabenzonorbornadienes

Jamie Haner
Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, ON, N1G 2W1, Canada, Fax: +1(519)7661499   eMail: wtam@uoguelph.ca
,
Kelsey Jack
Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, ON, N1G 2W1, Canada, Fax: +1(519)7661499   eMail: wtam@uoguelph.ca
,
Michelle L. Menard
Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, ON, N1G 2W1, Canada, Fax: +1(519)7661499   eMail: wtam@uoguelph.ca
,
Jennifer Howell
Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, ON, N1G 2W1, Canada, Fax: +1(519)7661499   eMail: wtam@uoguelph.ca
,
Jaipal Nagireddy
Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, ON, N1G 2W1, Canada, Fax: +1(519)7661499   eMail: wtam@uoguelph.ca
,
Mohammed Abdul Raheem
Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, ON, N1G 2W1, Canada, Fax: +1(519)7661499   eMail: wtam@uoguelph.ca
,
William Tam*
Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, ON, N1G 2W1, Canada, Fax: +1(519)7661499   eMail: wtam@uoguelph.ca
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Publikationsverlauf

Received: 07. Mai 2012

Accepted after revision: 12. Juni 2012

Publikationsdatum:
11. Juli 2012 (online)

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Abstract

Oxabenzonorbornadienes are valuable synthetic intermediates because they can serve as a general template with which to create highly substituted ring systems. However, to date, only very few C1-substituted oxabenzonorbornadienes have been reported. In this study, the synthesis of some C1-substituted oxabenzonorbornadienes was achieved by the Diels–Alder reaction between 2-substituted furans and benzyne. Moderate to good yields (16–80%) of the Diels–Alder reactions were observed. These C1-substituted oxabenzonorbornadienes will find applications as valuable synthetic intermediates and should be useful in studies of transition-metal-catalyzed reactions.

Key words

cycloaddition - Diels–Alder reaction - benzyne - furan - alkenes