SummaryThe chemical behaviour of various alkyl-substituted, acyclic conjugated bisallenes in reactions involving polar intermediates and/or transition states has been investigated on a broad scale for the first time. The reactions studied include lithiation, reaction of the thus formed organolithium salts with various electrophiles (among others, allyl bromide, DMF and acetone), oxidation to cyclopentenones and epoxides, hydrohalogenation (HCl, HBr addition), halogenation (Br2 and I2 addition), and [2 + 2] cycloaddition with chlorosulfonyl isocyanate. The resulting adducts were fully characterized by spectroscopic and analytical methods; they constitute interesting substrates for further organic transformations.

Key indicatorsSingle-crystal X-ray study T = 178 K Mean '(C±C) = 0.003 A Ê R factor = 0.042 wR factor = 0.115 Data-to-parameter ratio = 24.9For details of how these key indicators were automatically derived from the article, see

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.

The mol­ecule of the title compound, C10H14, displays inversion symmetry. The allenic bond lengths are 1.3067 (16) and 1.3126 (16) Å.

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