Small-Ring Compounds. IX. The Reaction of Silver Cyclobutanecarboxylate with Iodine

Cyclobutanol was first reported by Perkin in 1894 as the product of the reaction between cyclobutylamine and nitrous acid. However, it was later shown that Perkin's material was actually a mixture of roughly equal amounts of cyclobutanol and cyclopropylcarbinol along with a small amount of allylcarbinol. In 1907, Demjanow and Dojarenko reported the synthesis of presumably authentic cyclobutanol by hydrolysis of cyclobutyl cyclobutanecarboxylate obtained from the reaction of silver cyclobutanecarboxylate with iodine or the electrolysis of potassium cyclobutanecarboxylate.