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 ...
