Issue 6, 1976
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Orientation of a bridged quinone system. An intramolecular photochemical cyclisation giving a cyclobutane ring, and a novel simulation by non-photochemical means

Francis M. Dean,   Gordon H. Mitchell,   Bahman Parvizi  and  Chachanat Thebtaranonth (née Patamopongse)  

Abstract

A reinvestigation of the n.m.r. spectrum of the bridged quinone derivative (IVb) confirms that Meƒ is correctly placed at position 11a. In support, position 7b must carry a hydrogen atom, because acid-catalysed acetylation opens the bridge and ring B can then aromatise giving the quinol hemiacetal triester (IX).

Unlike the phenol(IVa) previously examined, its acetate (IVb) is slowly transformed in daylight into the cyclobutane derivative (VIIb). Remarkably, the propionate is much more sensitive to light. Also remarkably, esterification of the phenol (IVa) by propionic anhydride and pyridine generates some of the cyclobutane derivative (VIIg) even in darkness, although pyridine fails to induce cyclobutane ring formation in the (pre-formed) bridge propionate (IVg).

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Article information

DOI
https://doi.org/10.1039/P19760000595
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1976, 595-599

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Orientation of a bridged quinone system. An intramolecular photochemical cyclisation giving a cyclobutane ring, and a novel simulation by non-photochemical means

F. M. Dean, G. H. Mitchell, B. Parvizi and C. T. (née Patamopongse), J. Chem. Soc., Perkin Trans. 1, 1976, 595 DOI: 10.1039/P19760000595

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