Issue 8, 1989
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

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

Eiji Ōsawa,   Dora A. Barbiric,   Oh Seuk Lee,   Yukishige Kitano,   S. Padma  and  Goverdhan Mehta  

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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Article information

DOI
https://doi.org/10.1039/P29890001161
Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1989, 1161-1165

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

E. Ōsawa, D. A. Barbiric, O. S. Lee, Y. Kitano, S. Padma and G. Mehta, J. Chem. Soc., Perkin Trans. 2, 1989, 1161 DOI: 10.1039/P29890001161

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