ChemInform Abstract: STUDIES ON AMINES AND AMMONIUM COMPOUNDS. CLV. STEVENS REARRANGEMENT INVOLVING A METHYL‐SUBSTITUTED CARBALKOXYMETHYL GROUP

Kocharyan, S. T.; Grigoryan, Valeri G.; Voskanyan, V. S.; Panosyan, G. A.; Babayan, A. T.

doi:10.1002/chin.198202111

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2004

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“…We earlier showed that the methoxycarbonylmethyl analog of aminoester IIl undergoes thermal isomerization to form a 1,2-Stevens rearrangement product [7]. It was found that aminoester IIl is more susceptible to thermal isomerization than its methoxycarbonylmethyl analog, which appears to be explained by the steric effect of the ester tert-butyl group (Tables 2 and 3).…”

Section: äääääääääääämentioning

confidence: 97%

Stevens rearrangement of ammonium salts containing 2-propynyloxy or tert-butoxycarbonylmethyl groups

et al. 2004

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The Stevens rearrangement of ammonium salts containing 2-alkenyl, 2-alkynyl, or benzyl groups along with 2-propynyloxy or tert-butoxycarbonylmethyl was studied. Under the action of a suspension of sodium phenolate in benzene the salts containing a 2-propynyloxycarbonylmethyl group form 2-propynyl esters of 2-dialkylamino-4-pentenoic acids, whereas with sodium methylate as the basic reagent, rearrangement is preceded by an almost complete transesterification. The salts containing a tert-butoxycarbonylmethyl group undergo almost no transesterification under the action of sodium methylate. The tert-butyl fragment in the ester group of the salt with a benzyl group exerts a fairly strong effect on the regiochemistry of the rearrangement and on the prototropic isomerization of the 3,2-Stevens rearrangement of the salts with 2-butynyl or 3-phenyl-2-propynyl groups.

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Section: äääääääääääämentioning

confidence: 97%