All Questions
Tagged with organoboron-compounds organic-chemistry
16
questions
-1
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In hydroboration oxidation reaction .. why do not we use sodium hydroxide alone as a nuclophile?
Why do not we use sodium hydroxide alone as a nuclophile instead of using hydrogen peroxide along with sodium hydroxide
1
vote
1
answer
98
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Hydroboration–oxidation reaction without THF
The first step of hydroboration–oxidation usually involves $\ce{BH3}$ accompanied by THF. Is it possible for hydroboration to occur without the presence of THF? Borane is incredibly reactive. Wouldn't ...
- 19
4
votes
0
answers
61
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Purpose of "1H" in naming of substituted heterocyclic compouns [duplicate]
I had a curious thought about the following molecule's name:
For such a simple molecule it seemed awfully complicated. From what I gathered, the "[c][1,2]oxaborinin-1-ol" stems from the ...
- 1,145
2
votes
0
answers
80
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Regioselectivity of hydroboration-oxidation of enol ethers
In the book Hydroboration and Organic Synthesis, on p. 99, it is written that:
hydroboration [of enol ethers] proceeds regioselectively, placing essentially all of the boron atoms at the β position
...
- 10.7k
1
vote
0
answers
36
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Hydroboration, steroselectivity and anti-markovnikov product [duplicate]
My first question has to do with the fact that Hydroboration produces an anti-markovnikov product, why?. I don't see how that happens. A wikipedia artical says that B has a partial positive charge ...
- 11
3
votes
0
answers
57
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I need to reduce the Nitrile group without affecting the boronic acid. How to do that?
I need to Reduce the Nitrile group (CN) in the (3-cyanophenyl)boronic acid in to a primary amine without disturbing the Boronic acid group.Using LAH can trigger reduction of Boronic group. what are my ...
6
votes
2
answers
713
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What is the mechanism for the reaction of alkenes with diborane and chloramine?
$$\ce{CH3-CH=CH2 ->[B2H6/THF][NH2Cl/H2O, Δ] Product (P)}$$
What is $\ce{Product (P)}?$
First of all, in this reaction I performed hydroboration to form an alkylborane. But I don't have any ideas ...
- 153
4
votes
0
answers
282
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Rationalise the Relative Reactivity of Borane and DIBAL as Reductants
In Clayden's Organic Chemistry (Second Edition) it is written that borane is useful in chemoselectively reducing the most nucleophilic carbonyl to its corresponding alcohol. It is later said that ...
- 884
15
votes
1
answer
13k
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What happens when an alkylborane is treated with acetic acid?
In the hydroboration reactions of alkenes I've seen so far, they were always followed by oxidation with $\ce{H2O2/NaOH}$ (to yield alcohols).
Today I found a peculiar reaction in which acetic acid-...
- 2,209
3
votes
1
answer
342
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Why is an alkoxide released instead of hydroxide in the attack of trialkyloxyborane by hydroxide?
In the mechanism of a hydroboration-oxidation, the oxidation part includes a nucleophilic attack of a hydroxide on a trialkyloxyborane ( $\ce{B(OR)_3}$ where $\ce{R}$ is an alkyl group).
It creates ...
- 1,441
11
votes
1
answer
2k
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Why does boron add to the less substituted carbon in the hydroboration of an alkene?
In the hydroboration of a typical alkene, the boron fragment ends up attached to the less substituted carbon:
What are the electronic or steric factors that lead to this regioselectivity?
- 1,024
10
votes
2
answers
6k
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Is 1,2-dihydro-1,2-diborete aromatic?
What kind of aromaticity does 1,2-dihydro-1,2-diborete have?
I read somewhere that 1,2-dihydro-1,2-diborete is an aromatic compound, but I believe that in order to be aromatic, it should have a ...
- 191
17
votes
1
answer
4k
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Why is 1H-borepine aromatic?
For a compound to be aromatic, each atom in the ring must be a part of conjugation. Boron here has no lone pair, so how can 1H-borepine be aromatic as I was told by someone?
- 4,197
2
votes
0
answers
641
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Selectivity in Suzuki coupling of 2,4-dichloropyrimidine
I've seen many papers (see e.g. Synthesis 2010, 16, 2721–2724) in which the 4-chloro group of 2,4-dichloropyrimidine is selectively reacted under Suzuki coupling conditions. Is there any way where ...
- 21
2
votes
1
answer
4k
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What is the stereochemistry resulting from hydroboration of 1-methylcyclopentene?
What is the major product of the following reaction sequence?
I'm supposed to work out the structures of both 2 and 3, but I already know 2 to be 1-methylcyclopentene (as the most substituted ...
- 507