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Surya Prakash Rao", "name": "H. Surya Prakash Rao", "type": "personal" } }, { "person_or_org": { "family_name": "K. Jeyalakshmi", "name": "K. Jeyalakshmi", "type": "personal" } }, { "person_or_org": { "family_name": "8. Bharathi", "name": "8. Bharathi", "type": "personal" } }, { "person_or_org": { "family_name": "L. Pushpalatha", "name": "L. Pushpalatha", "type": "personal" } }, { "person_or_org": { "family_name": "V. Umamaheswari", "name": "V. Umamaheswari", "type": "personal" } } ], "description": "

Department of Chemistry, Pondicherry University, Pondicherry-605 014, India

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E-mail : hspr@satyam.net.in I hspr@yahoo.com

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Manuscript received 16 October 2001

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The simple reaction of chalcones with cyclopentanone in the presence of barium hydroxide furnished complex domino products of the types 4 and 5 along with 1,5-diketones 3. Mechanistic considerations reveal that the bicyelic alcohol 4 was formed by sequential Michael-Michael-aldol reactions involving two moles of chalcone and one mole of cyclopentanone. Whereas, formation of spiro-bicyclic diol 5 involved sequential Michael-1,2-addition-aldol condensation involving one mole of chalcone and two moles of cyclopentanone. Formation of the domino products was found to be critically dependent on electronic finetuning in the both the aromatic rings.

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