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spiropentadiene : ウィキペディア英語版
spiropentadiene

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Spiropentadiene, or bowtiediene, is a hydrocarbon with formula C5H4. The simplest spiro-connected cycloalkene, it is very unstable—decomposing even below −100 °C—due to its high bond strain and does not occur in nature. Its synthesis was reported in 1991.〔''Elusive bowtie pinned down - synthesis of spiropentadiene, a carbonaceous compound nicknamed bowtiediene because it is shaped like a bowtie'', ''Science News'', July 13, 1991.〕
==Synthesis==
Spiropentadiene was synthesised from bistrimethylsilylpropynone 1 by reaction with p-toluenesulfonylhydrazide to tosylhydrazone 2 followed by treatment with sodium cyanoborohydride to allene 3 and followed by two successive reactions with chlorocarbene generated from methyllithium and dichloromethane to spiro compound 5. Spiropentadiene was trapped in a liquid nitrogen trap after reaction with TBAF in a double elimination reaction.
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抄文引用元・出典: フリー百科事典『 ウィキペディア(Wikipedia)
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