1,4-Bishomo[6]prismane (garudane): molecular structure and strain analysis of reactions potentially leading to prismanes

Osawa, Eiji O ; Barbiric, Dora A. ; Seuk Lee, Oh ; Kitano, Yukishige ; Padma, S. ; Mehta, Goverdhan (1989) 1,4-Bishomo[6]prismane (garudane): molecular structure and strain analysis of reactions potentially leading to prismanes Journal of the Chemical Society, Perkin Transactions 2 . pp. 1161-1165. ISSN 0300-9580

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Official URL: http://www.rsc.org/publishing/journals/article.asp...

Related URL: http://dx.doi.org/10.1039/P29890001161

Abstract

The proposed structure of garudane (1), the face-to-face D2h dimer of norbornadiene, has been confirmed by the X-ray analysis of a single crystal of the 1,3-bis(methoxycarbonyl) derivative (2), monoclinic, space group C2/c, a= 16.570(6), b= 8.073(4), c= 12.151(4)Å,β = 114.89(2)°, final R= 0.055, Rw= 0.070. Detailed structural characteristics observed for (2) are compared with the isomeric D2d dimer (isogarudane)(3). Compound (1) is calculated to be 44 kcal mol-1 mere strained than (3). The demethylenation procedure on (1)-and the 1,4-bis homo[7] prismane (10) of similar structure-as a potential synthetic route to [6]- and [7]-prismanes (4) and (5) has advantages over the intramolecular [2+2]-photocyclization of polycyclic dienes [e.g.(12) and (13)] and the pinacolic coupling of polycyclic diketones [e.g.(14)]. These are discussed on the basis of strain analysis.

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