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26.2.1.5.2 Variation 2: Of 2,2-Dichlorocyclobutanones

DOI: 10.1055/sos-SD-026-00397

Salaün, J.Science of Synthesis, (200526563.

By using either zinc dust in acetic acid[‌26‌] or tributyltin hydride[‌27‌] one or two chlorine atoms are easily and selectively removed from α,α-dichlorocyclobutanones.[‌28‌] Thus 7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one (31), formed by [2+2] cycloaddition of dichloroketene to cyclopentene (see Section 26.2.1.7.2), is reduced by zinc/acetic acid to yield bicyclo[3.2.0]hept-2-en-6-one (33) in 95% yield via the endo-monochloro adduct 32 (Scheme 12).[‌28‌]

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