「カルボニル還元」の版間の差分

The [[Rosenmund reduction|Rosenmund reaction]] reduces acyl chlorides to aldehydes using hydrogen gas with a catalyst of palladium on barium sulfate, whose small surface area prevents over-reduction.<ref>{{Cite book|title = The Rosenmund Reduction of Acid Chlorides to Aldehydes|publisher = John Wiley & Sons, Inc.|date = 2004-01-01|isbn = 9780471264187|doi = 10.1002/0471264180.or004.07|first = Erich|last = Mosettig|first2 = Ralph|last2 = Mozingo}}</ref> For more reactive substrates, the catalyst must be further hindered with a poison, often one containing sulfur.
 
== アルデヒド、ケトンとアルケン ==
== Aldehydes and ketones to alkanes ==
[[File:Wolff-kishner mechanism.png|thumb|378x378px|Mechanism of Wolff-Kishner reduction[[ウォルフ・キシュナー還元]]の反応機構]]
Aldehydes and ketones can be reduced not only to alcohols but also to alkanes. Some reactions for this transformation include the アルデヒドとケトンはアルコールだけでなくアルカンまで還元することもできる。この変換反応には強酸性下で起こる[[Clemmensen reductionクレメンセン還元]] (in strongly acidic conditions) and the や強塩基性下で起こる[[Wolff–Kishner reduction|Wolff-Kishner reductionウォルフ・キシュナー還元]] (in strongly basic conditions), as well as the various [[Wolff–Kishner reductionおよびその派生などが含まれる。例えば{{仮リンク|modifications of the Wolff-Kishner reaction]]. Theヴィンセンツォ・カリオリティ|en|Vincenzo Caglioti modification, for instance, uses [[|label=カリオリティ}}の開発した反応では、{{仮リンク|トシルヒドラゾン|en|tosylhydrazone]] with a hydride donor in milder conditions with no base;}}とヒドリド供与体を利用することで、塩基を使わず穏和な条件下で反応を進めることができる<ref>{{Cite journal|title = The reaction of tosylhydrazones with lithium aluminium hydride|url = http://www.sciencedirect.com/science/article/pii/S0040402001985710|journal = Tetrahedron|date = 1963-01-01|pages = 1127–1131|volume = 19|issue = 7|doi = 10.1016/S0040-4020(01)98571-0|first = L.|last = Caglioti|first2 = M.|last2 = Magi}}</ref> the Myers modification substitutes hydrazine with bis。マイアズによって報告された反応では、置換[[ヒドラジン]]をビス([[tert-butyldimethylsilylブチルジメチルシリル基|tert-ブチルジメチルシリル]])-hydrazine, uses milder conditions at room temperature, and is rapid and efficient.ヒドラジンと室温下の穏和な条件で反応させ、[[反応速度|速く]]かつ高収率で還元できる<ref>{{Cite journal|title = Practical Procedures for the Preparation of N-tert-Butyldimethylsilylhydrazones and Their Use in Modified Wolff−Kishner Reductions and in the Synthesis of Vinyl Halides and gem-Dihalides|journal = [[米国化学会誌|Journal of the American Chemical Society]]|date = 2004-05-01|issn = 0002-7863|pages = 5436–5445|volume = 126|issue = 17|doi = 10.1021/ja049694s|first = Michael E.|last = Furrow|first2 = Andrew G.|last2 = Myers|pmid=15113215}}</ref>
 
=={{anchor|1.2C4-reduction}}α,β-unsaturated carbonyls==