Alkine und Cumulene, XXIII. über einige Neben‐ und Folgeprodukte der Dichlorketen‐Herstellung aus α,α‐Dichloracetylchlorid

Abstract

Alkynes and Cumulenes, XXIII. – On Some Byproducts of the Dichloroketene Preparation from α,α‐Dichloroacetyl Chloride When α,α‐dichloroacetyl chloride (1) is dehydrochlorinated with triethylamine in refluxing ether, two oligomers are obtained: 1‐dichloroacetoxy‐1‐dichloromethyl‐2,2‐dichloroethylene (3) and octachloro‐1,2‐bis(methylene)cyclobutane (4). The mechanisms of formation of these tri‐ and tetrameric products of 1 and dichloroketene (2), respectively, are discussed, and an X‐ray structural analysis of 4 is reported.

Decachlorohexa-1,5-diene

“…For the synthesis of perchloroalkenes, see: Prins (1949); Roedig et al (1963). For structures of perchloroalkenes, see: Herbstein (1979); Rao & Livingston (1958); Hopf et al (1991); Detert et al (2009). For rearrangements of highly halogenated alkenes, see: Maahs (1963); Herges et al (2005).…”