Science of Synthesis

Tidwell, T. T., Science of Synthesis, (2006) 23, 579.

The cleavage of cyclobutanones to form ketenes is useful in selected examples, particularly in the cleavage of strained derivatives. Thus oxidation of exo-bicyclo[2.2.0]hexan-2-ol (‌50‌) with tert-butyl hypochlorite (‌51‌) gives bicyclo[2.2.0]hexan-2-one (‌52‌) as a transient intermediate that cannot be isolated but can be detected by the presence of an IR band at 1782 cm–1.[‌59‌] When the reaction is conducted in carbon tetrachloride in the presence of pyridine, hex-5-enoic acid (‌54‌) and exo-bicyclo[2.2.0]hex-2-yl hex-5-enoate (‌55‌) are isolated in 30 and 23% yields, respectively. The formation of these products confirms that the bicycloalkanone ‌52‌ undergoes ring opening to form (but-3-enyl)ketene (‌53‌) (‌Scheme 16‌).[‌59‌] The reaction was originally conducted for a period of three months in a sealed vial, but it has not been established if such a long a period is necessary.

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References

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• 8.Meeeee-Meee, (8888) M 88-8, 8888.