Journal Title
Title of Journal: J Chem Sci
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Abbravation: Journal of Chemical Sciences
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Authors: SAMBASIVARAO KOTHA SHAIBAL BANERJEE MOBIN SHAIKH
Publish Date: 2014/11/04
Volume: 126, Issue: 5, Pages: 1369-1371
Abstract
The bond length between C8C9 in 1′ R4′ S4a′ R8a′ S6′7′dimethyl1′4′4a′8a′tetrahydrospiro cyclopropane19′14methanonaphthalene5′8′dione is 1571 2 Å and between C7C12 is 1567 2 Å which are longer than the corresponding bond length for saturated bicyclic systems 15311535 Å This paper reports the correlation between bond length and the ease of retro Diels −Alder reactionWe examined the crystal structure of 1′R4′S4a′R8a′S6′7′dimethyl1′4′4a′8a′tetrahydrospirocyclopropane19′14 methano naphthalene5′8′dione and found that the bond length between atoms connecting diene and the dienophile is somewhat longer than the normal C–C bond length The increased bond length is responsible for the facile rDA reaction of 5We would like to acknowledge the DST New Delhi for the financial support We also thank SAIFMumbai for recording the spectral data S K thanks DST New Delhi for the award of a J C Bose fellowship S K thanks Darshan Mhatre for his help regarding Xray data collectionXray diffraction data were collected on an OXFORD XCALIBURS CCD singlecrystal Xray diffractometer The structure was solved and refined by fullmatrix leastsquares techniques on F2 using the SHELX97 program Sheldrick 1997 Crystallographic data excluding structure factors for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication Compound 5CCDC 958630 Copies of available material can be obtained free of charge on application to the CCDC 12 Union Road Cambridge CB2 1EZ UK email depositccdccamacuk
Keywords:
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