The constitution of umbellulone. [Pt. I] / by Frank Tutin.

  • Tutin, Frank.
Date:
[1906]
Catalogue details

Licence: Attribution 4.0 International (CC BY 4.0)

Credit: The constitution of umbellulone. [Pt. I] / by Frank Tutin. Source: Wellcome Collection.

Provider: This material has been provided by The Royal College of Surgeons of England. The original may be consulted at The Royal College of Surgeons of England.

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    OH-COgH OH CO Me-CH CHg CH2-CH-CO-CH3 Umbellulouic acid. Me-CH CHj O CH2-CH c:ch2 The lactone. CH-COgH Me-CH CH2 CH2-CH-C02H Umbellularic acid. The above constitutional formula offers a ready explanation of the behaviour of umbellulone on treatment with bromine and subsequent distillation of the product. The liquid obtained by the treatment of umbellulone with bromine represents the compound formed by the direct addition of the halogen to the carbon atoms of the ethylenic linking. This compound, on distillation, eliminates hydrogen bromide in two ways : OH2 CH CO CHg CH CO I /CH2-CHMe I -HBrgivesI /OH2-CHMe | ^nd OH CBr(Me)-CHBr CH C:(CH2)-CHBr I. CH2 CH CO |^.CH2-CHMe I C====C(Me)*CHBr II. One of these unsaturated compounds (probably II) is incapable of recombining with the hydrogen bromide, and represents the mono- bromoumbellulone. The other compound immediately unites with the elements of hydrogen bromide, and yields the solid dibromodihydro- umbellulone, which is therefore probably represented by the formula CH2 CH CO I /CH2-CHMe I CH CH(CH2Br)*CHBr The saturated ketone, Oj^H^gO (m. p. of semicarbazone, 177°), obtained by Lees by the reduction of monobromoumbellulone, CjgH^gOBr, and which it is proposed to name a dihydroumbellulone, will therefore be represented by the formula CHg CH CO I yCHg-CHMe I CH CHMe-CHg 'ihe reduction of umbellulone itself with sodium and alcohol and