Synthesis and deamination of a deuterium-labeled spiropentylamine

DE Applequist, MR Johnston…

Index: Applequist,D.E. et al. Journal of the American Chemical Society, 1970 , vol. 92, p. 4614 - 4617

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Citation Number: 11

Abstract

Abstract: Spiropentylamine has been synthesized with a deuterium label in the 4 position. Nitrous acid deamination has yielded 2-and 3-methylenecyclobutanols with deuterium distributed such as to suggest a mechanism involving initial ring enlargement or bicyclobutonium ion formation. Comparison is made with hydrolysis of spiropentyl chloride, which gives Z-hydroxymethyl-l, 3-butadiene as the major product. revious work in this ...

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