Synthesis 2008(12): 1883-1888  
DOI: 10.1055/s-2008-1067100
PAPER
© Georg Thieme Verlag Stuttgart · New York

Dipolar Cycloaddition of Dicyclopentadiene with 3-Oxidopyrylium Betaine: An Entry into Methano-Bridged 5-6-7-Fused Ring System

Arun A. Yadava, Prajakta S. Saranga, Chaitanya S. Wannereb, Girish K. Trivedi*a, Manikarao M. Salunkhe*c
a Department of Chemistry, The Institute of Science, 15, Madam Cama Road, Mumbai 400032, India
b Department of Chemistry, University of Georgia, Athens, GA 30602, USA
c Department of Chemistry, Shivaji University, Vidyanagar, Kolhapur 410006, India
Fax: +91(231)2691533; e-Mail: mmsalunkhe@hotmail.com; e-Mail: snehgkt@yahoo.com;
Further Information

Publication History

Received 9 January 2008
Publication Date:
16 May 2008 (online)

Abstract

The [3+2] cycloaddition of 3-oxidopyrylium ylide, generated from an acetoxypyranone, proceeds with complete chemo- and stereoselectivity. The approach of the dipole takes place exclusively from the exo-face of the bicycloheptane moiety providing a mixture of regioisomers in approximately 55:45 ratio. The derived cycloadduct is then transformed to a novel syn-anti-cis-condensed methano-bridged molecular entity.

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9

Selected X-ray crystallographic data for 7 (C15H16O2): space group: orthorhombic, Pbna; unit cell dimensions: a = 7.7630 (18) Å, b = 12.0930 (5) Å, c = 24.0210 (14) Å; V = 55.0(5) Å3; Z = 8, D calc = 1.345 Mg/m-3; absorption coefficient = 0.088 mm-1. Complete crystallographic data (excluding structure factors) for this structure have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 679327. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (1223)336033 or e-mail: deposit@ccdc.cam.ac.uk].

13

Selected X-ray crystallographic data for 14a (C17H20O3): unit cell contains two molecules, for simplicity only one molecule is shown in Figure [3] ; space group: monoclinic P21/c; unit cell dimensions: a = 10.2468 (16) Å, b = 8.7716 (12) Å, c = 31.016 (8) Å; V = 2748.1 (9) Å3; Z = 4, D calc = 1.316 Mg/m-3; absorption coefficient = 0.089 mm-1. Complete crystallographic data (excluding structure factors) for this structure have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 679328. Copies of the data can be obtained, free of charge, on application to CCDC.