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 2-hydroxymethyl-1,3-butadiene as the major product.
Previouswork in this laboratory1 has shown that the nitrous acid deamination of spiropentylamine (1) gives mainly the methylene cyclobutanols, 2 and 3. 1 HXO,.
Das Spiropentan (III) wird aus dem Cyclopropan (I) mit der Hg‐Verbindung (II) dargestellt und mit dem Butylzinn (IV) zum markierten Spiropentan (V) umgesetzt.
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