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1-Decene hydroboration-oxidation

With this as introduction, let us now look at the individual steps in more detail for the case of hydroboration-oxidation of 1-decene. A boron hydride that is often used is dibomne (B2H6). Diborane adds to 1-decene to give tridecylborane according to the balanced equation ... [Pg.251]

Rationalizations of hydroboration stereoselectivity using models with dimeric boranes are thus not viable. Recent secondary isotope-effect measurements may suggest a model (Mann et al., 1986). Addition of a chiral dialkyl borane to 3-deuterio-cw-3-pentene, followed by alkaline oxidation, yields equal amounts of 3- and 4-deuterio-3-hexanols showing that the secondary isotope effects at these alkene sites are vanishingly small. Deuterium substitution at the allylic sites has a much larger effect. Thus similar treatment of 4,4-dideuterio-cw-5-decene yields a 2.86 1 mixture of 4,4-dideuterio- and 6,6-dideuterio-5-decanols. [Pg.66]

Hydroboration of isoprene with catecholborane at 1 1 molar ratio in tetrahydrofliran in the presence of 1 molar % of NiCbCdppe) at room temperature was completed in 6 h. An interesting observation is a lower reactivity of 1-decene compared with isoprene under these conditions. It is the first case of higher reactivity of 1,3-diene than 1-alkene in the hydroboration reaction. It is also an indirect indication that borane is not involved in the reaction, since acyclic conjugated dienes are less reactive than 1-alkenes toward borane. Hydroboration of representative conjugated dienes in the presence of NiCUCdppe) was carried out on a preparative scale and the results are shown in Table 2.9 The mono-hydroboration products were isolated by distillation and oxidized to the corresponding unsaturated alcohols. [Pg.418]

Recently it has been found that the speed of addition of diborane to olefins is remarkably increased if an ether is present (21). In spite of its great speed this hydroboration reaction in ether is fairly selective. Thus treatment of an equimolar mixture of 1- and 2-hexene with a deficiency of diborane, followed by refluxing, yielded tri-n-hexylboiane. Under the influence of heat the organoborane from 2-hexene isomerized into tri-n-hexylbornne (22). Similarly a mixture of 2-, 3-, 4-, and 5-decenes treated with diborane in ether, heated and then subsequently oxidized gave an 80% yield of 1-decanol. Diborane may thus be used to transform olefins into alcohols. [Pg.302]


See other pages where 1-Decene hydroboration-oxidation is mentioned: [Pg.251]    [Pg.268]    [Pg.286]    [Pg.1569]    [Pg.1568]    [Pg.314]   
See also in sourсe #XX -- [ Pg.250 , Pg.626 ]




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1 Decene

2-Decen

2-Decenal

Decenes

Decenes 1-decene

Hydroboration oxidation

Oxidative hydroboration

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