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hydrogenolysis
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hydrogenolysis
hydrogenolysis Chem. (ˌhaɪdrədʒəˈnɒlɪsɪs) [f. hydrogen + -o + lysis, after hydrolysis.] The splitting of a bond accompanied by the addition of an atom of hydrogen to the atoms originally bonded (one or both of these being carbon atoms).1931 C. Ellis Hydrogenation Org. Subst. xlv. 522 For reasons of ...
Oxford English Dictionary
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Hydrodeoxygenation
Hydrodeoxygenation (HDO) is a hydrogenolysis process for removing oxygen from oxygen-containing compounds.
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5,6-Dihydroxyindole
This compound is condensed with nitromethane in a Henry reaction, followed by nitration, reduction of the nitro groups, and hydrogenolysis of the benzyl
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-lysis
-lysis (lɪsɪs) A word-forming element [f. Gr. λύσις a loosening, parting] in many technical terms, primarily denoting decomposition, disintegration, dissolution. 1. In words in which the first element indicates the agent; e.g. (in Chem.) electrolysis (c 1840), hydrogenolysis; (in Biol.) bacteriolysi...
Oxford English Dictionary
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Hydrodesulfurization
The net result of a hydrogenolysis reaction is the formation of C-H and H-X chemical bonds. Thus, hydrodesulfurization is a hydrogenolysis reaction. Other uses
The basic hydrogenolysis reaction has a number of uses other than hydrodesulfurization.
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2-Methylfuran
Manufacture
2-Methylfuran is an article of commerce (chemical intermediate) and is normally manufactured by catalytic hydrogenolysis of furfural alcohol or via a hydrogenation-hydrogenolysis sequence from furfural in the vapor phase.
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Sorbose
Hydrogenolysis removes the four benzyl groups, leaving sorbose.
References
Ketohexoses
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1,5-Pentanediol
It can also be prepared by hydrogenolysis of tetrahydrofurfuryl alcohol.
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بنزيلامين
الاستعمالات
يتم استخدامه كمصدر مانع من الامونيا، منذ بعد N - عملية الألكلة، مجموعة البنزيل يمكن إزالتها عن طريق hydrogenolysis:
C6H5CH2NH2 + 2 RBr
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Benzyl group
For related reasons, benzylic substituents exhibit enhanced reactivity, as in oxidation, free radical halogenation, or hydrogenolysis. Removed using hydrogenolysis
Single electron process with Na/NH3 or Li/NH3
Benzyl protecting groups can be removed using a wide range of oxidizing
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P-Toluic acid
It is generated both by the oxidation of p-xylene as well as the hydrogenolysis of 4-carboxybenzaldehyde.
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N-Methylmorpholine
It is produced by the reaction of methylamine and diethylene glycol as well as by the hydrogenolysis of N-formylmorpholine.
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Protecting group
Trityl (triphenylmethyl, Tr) – Removed by acid and hydrogenolysis. p-Methoxybenzyl (PMB) – Removed by hydrogenolysis, more labile than benzyl
3,4-Dimethoxybenzyl (DMPM) – Removed by hydrogenolysis, more labile than p-methoxybenzyl
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Palladium on carbon
Hydrogenolysis
Palladium on carbon is a common catalyst for hydrogenolysis. Such reactions are helpful in deprotection strategies. Particularly common substrates for hydrogenolysis are benzyl ethers:
Other labile substituents are also susceptible to cleavage by this reagent.
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Transition metal alkoxide complex
Hydrogenolysis
The metal-alkoxide bond is susceptible to hydrogenolysis, especially for platinum metal derivatives:
Illustrative alkoxides
References
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