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23.14.1.1.5.1 Variation 1: Photolysis of Cyclobutanones

DOI: 10.1055/sos-SD-023-00535

Tidwell, T. T.Science of Synthesis, (200623581.

Photolysis of the endo-fused cyclobutanone 64 gives the ketene 65, identified by its IR absorption at 2155cm1, which is captured by methanol to give the ester 66 in 57% yield (Scheme 19).[‌63‌] The corresponding exo-isomer similarly gives the ester 66, but in only 10% yield.[‌63‌] A less-strained cyclobutanone fused to a bicyclooctene ring gives little ketene formation upon photolysis.[‌63‌]

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