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・ Teruji Kogake
・ Terukazu Tanaka
・ Teruki Miyamoto
・ Teruki Tabata
・ Teruki Tanaka
・ Terukkuttu
・ Teruko
・ Teruko Oe
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・ Terukuni jinja
・ Tert-Butylamine
・ Tert-Butyldiphenylsilyl
・ Tert-Butylhydroquinone
・ Tert-Butyllithium
・ Tert-Butyloxycarbonyl protecting group
Tert-Butylphosphaacetylene
・ Tert-Butylthiol
・ Tert.am
・ Tertali
・ Tertangala
・ Tertatolol
・ Tertene Nunataks
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・ Terthreutis bipunctata


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Tert-Butylphosphaacetylene : ウィキペディア英語版
Tert-Butylphosphaacetylene

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''tert''-Butylphosphaacetylene is an organophosphorus compound. Abbreviated ''t''-BuCP, it was the first example of an isolable phosphaalkyne. Prior to its synthesis, the double bond rule had suggested that elements of Period 3 and higher were unable to form double or triple bonds with lighter main group elements because of weak orbital overlap. The successful synthesis of ''t''-BuCP discredited much of the double bond rule and opened new studies into the formation of unsaturated phosphorus compounds.
==Synthesis and reactions==
The synthesis of ''t''-BuCP entails the reaction of pivaloyl chloride and P(SiMe3)3. The reaction proceeds via the intermediacy of a bis(trimethylsilyl)pivaloylphosphine, which undergoes a 1,3-silyl shift to form E- or Z-phosphoalkene isomers. Carrying out the phosphoalkene reaction at 120-200 °C in the presence of catalytic amounts of solid NaOH forms the final ''t''-BuCP product.〔Becker, Gerd; Gresser, Gudrun; Uhl, Werner. "2,2-Dimethylpropylidinphosphan, eine stabile Verbindung mit einem Phosphoratom der Koordinationszahl 1." Zeitschrift fuer Naturforschung, Teil B:Anorganische Chemie, Organische Chemie 1981, 36, 16.〕
:Me3CC(O)Cl + P(SiMe3)3 → Me3CC(O)P(SiMe3)2 + Me3SiCl
:Me3CC(O)P(SiMe3)2 → Me3CCP + O(SiMe3)2

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