Issue 7, 1979

Synthesis and X-ray structure of a cyclopenta[d]furo[2,3-b]furan derivative from isomerisation of 3,4,4-triacetyl-2-methyl-cis-4,4a,5,7a-tetrahydrocyclopenta[b]pyran

Abstract

3,4,4-Triacetyl-2-methyl-cis-4,4a,5,7a-tetrahydrocyclopenta[b]pyran (3), obtained by reaction of tetra-acetyl-ethylene (1) with cyclopentadiene, was converted into a mixture of the trans-isomer (4) and 3,3a-diacetyl-2,7a-dimethyl-3aα,4,6aα,7aα-tetrahydro-3bαH-cyclopenta[d]furo[2,3-b]furan (5), a new heterocyclic system, whose structure was definitively established by an X-ray analysis. Crystals are orthorhombic, a= 15.824(5), b= 15.465(5), c= 11.129(4)Å, Z= 8, space group Pbca. The structure was solved by direct methods and refined by least squares to a final R of 0.073 for 1 665 observed reflections. Some aspects of the mechanism are discussed.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1979, 903-906

Synthesis and X-ray structure of a cyclopenta[d]furo[2,3-b]furan derivative from isomerisation of 3,4,4-triacetyl-2-methyl-cis-4,4a,5,7a-tetrahydrocyclopenta[b]pyran

G. Adembri, R. Cini, P. Orioli, R. Nesi and M. Scotton, J. Chem. Soc., Perkin Trans. 2, 1979, 903 DOI: 10.1039/P29790000903

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements