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Molecules 2001, 6(3), 194-202; doi:10.3390/60300194
Article

7-(1-Acetoxymethylidene)Benzonorbornadiene: A Versatile Reagent for the Synthesis of 7-Formyl and 7-Hydroxymethyl Benzonorbornadienes

* ,  and
Centre for Molecular Architecture, Central Queensland University, North Rockhampton, 4701, Queensland, Australia
* Author to whom correspondence should be addressed.
Received: 30 November 2000 / Revised: 16 January 2001 / Accepted: 16 January 2001 / Published: 28 February 2001
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Abstract

7-(1-Acetoxymethylidene)benzonorbornadiene 3, prepared in one step by the addition of benzyne to 6-acetoxyfulvene 2, is hydrolysed in acid solution to form a 3:2-epimeric mixture of syn- and anti- 7-formylbenzonorbornadienes 4 and 5, respectively; the corresponding 7-hydroxymethylbenzonorbornadienes 6 and 9 were produced by reduction of the formyl isomers with sodium borohydride.
Keywords: Benzyne; cycloaddition; enolacetates; fulvenes; benzonorbornadienes Benzyne; cycloaddition; enolacetates; fulvenes; benzonorbornadienes
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Warrener, R.N.; Collin, G.J.; Foley, P.J. 7-(1-Acetoxymethylidene)Benzonorbornadiene: A Versatile Reagent for the Synthesis of 7-Formyl and 7-Hydroxymethyl Benzonorbornadienes. Molecules 2001, 6, 194-202.

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