Crystal Structure of a Cyclotetramer from a Strained Cyclic Allene

Crystal Structure of a Cyclotetramer from a Strained Cyclic Allene

The low-temperature treatment of 1,1-dibromo-1a,9b-cyclopropa[l]phenanthrene (1) with butyllithium and copper(II) chloride in THF affords a dibenzoannellated 1,2,4,6-cycloheptatetraene which undergoes a rare cyclotetramerization. The crystal structure of this “formal” 2 + 2 + 2 + 2 cyclotetramer (2)...

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Veröffentlicht in:Organic letters 2009-11, Vol.11 (22), p.5095-5097
Hauptverfasser: Mahlokozera, Tatenda, Goods, John B, Childs, Adam M, Thamattoor, Dasan M
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container_title Organic letters
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creator Mahlokozera, Tatenda
Goods, John B
Childs, Adam M
Thamattoor, Dasan M
description The low-temperature treatment of 1,1-dibromo-1a,9b-cyclopropa[l]phenanthrene (1) with butyllithium and copper(II) chloride in THF affords a dibenzoannellated 1,2,4,6-cycloheptatetraene which undergoes a rare cyclotetramerization. The crystal structure of this “formal” 2 + 2 + 2 + 2 cyclotetramer (2) reveals a central eight-membered ring folded in a zigzag fashion with hydrogen atoms and exocyclic double bonds occupying axial positions. B3LYP/6-31+G** calculations indicate that the strained cyclic allene is significantly distorted and could be formed by ring expansion of a putative cyclopropylidene intermediate.
doi_str_mv 10.1021/ol902177b
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title Crystal Structure of a Cyclotetramer from a Strained Cyclic Allene
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