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Synlett 2001; 2001(9): 1407-1410
DOI: 10.1055/s-2001-16778
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Novel Intermolecular [3 + 2] Cycloaddition Reaction of Carbonyl Ylides with Fulvenes: Entry into the Oxatetracyclo[6.5.1.01,6.09,13]tetradecene Ring System

Sengodagounder Muthusamy* , Srinivasarao Arulananda Babu, Chidambaram Gunanathan, Eringathodi Suresh, Parthasarathi Dastidar
  • *Silicates and Catalysis Discipline, Central Salt and Marine Chemicals Research Institute, Bhavnagar 364 002, India; Fax + 91 278 567562; E-mail: salt@csir.res.in (S. Muthusamy)
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Publikationsdatum:
28. August 2001 (online)

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Reaction of α-diazo carbonyl compounds 1/2 in the presence of rhodium(II) acetate dimer with pentafulvenes 3/6 generating the novel oxatetracyclo[6.5.1.01,6.09,13]tetradecene ring systems in good yield, is reported. In the presence of unsymmetrical and symmetrical fulvenes, the products were obtained as regioisomers in the ratio of 1 : 2 and 1 : 10, respectively. The sincle crystal X-ray analysis of compound 4b is reported to firmly establish the stereochemistry of regioisomers.

carbonyl ylides - cycloadditions - diazo carbonyl compounds - fulvenes - oxatetracyclic systems