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32.1.16 Product Subclass 16: 1,ω-Bis(heteroatom-functionalized) Cumulenes

DOI: 10.1055/sos-SD-032-00002

Hashmi, A. S. K.Science of Synthesis, (20083220.

Here a number of single representatives of the different subclasses are known: (Z)-1,4-dichloro-1,4-(di-4-tolyl)butatriene,[‌54‌] (Z)-4-bromo-1-chloro-1,4-(di-4-tolyl)butatriene,[‌54‌] 1,4-dinitro-1,4-diphenylbutatriene,[‌55‌] a porphyrin-like macrocyclic N,N-derivative,[‌56‌] (E)-1,4-diethoxybutatriene,[‌57‌] (Z)-1,4-diethoxybutatriene,[‌57‌] (E)-1,4-bis(tert-butyldimethylsiloxy)-2,2,7,7-tetramethylocta-3,4,5-triene,[‌58‌] (Z)-1,4-bis(tert-butyldimethylsiloxy)-2,2,7,7-tetramethylocta-3,4,5-triene,[‌58‌] 1,4-diisopropoxy-1,4-diphenylbutatriene,[‌59‌] 1-ethoxy-4-methoxybutatriene,[‌60‌] diethyl 4,7-diacetoxy-2,9-diacetyldeca-4,5,6-trienedioate,[‌61‌] 6,9-dibromotetradeca-6,7,8-triene,[‌62‌] 1,4-dibromo-1,4-diphenylbutatriene,[‌54‌,‌63‌] 1,4-dibromo-1,4-di-4-tolylbutatriene,[‌54‌,‌64‌] and 1ξ,4,5,6t-tetrabromo-1ξ,6c-diphenylhexa-1,2,3,5-tetraene.[‌65‌] None of the experimental procedures seems to have a broad synthetic scope.

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