Is HMgX also a Grignard Reagent like RMgX?
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We do know that the Grignard Reagent is $ce{RMgX}$ where R is some alkyl group & X is any halogen group.
So, my question is that, whether $ce{HMgX}$ is also a Grignard Reagent like $ce{RMgBr}$?
organic-chemistry grignard-reagent
edited Dec 8 at 12:24
Kelly Shepphard
63112
asked Dec 8 at 4:53
Ujjwal Sharma
291
add a comment |
up vote
5
down vote
favorite
We do know that the Grignard Reagent is $ce{RMgX}$ where R is some alkyl group & X is any halogen group.
So, my question is that, whether $ce{HMgX}$ is also a Grignard Reagent like $ce{RMgBr}$?
organic-chemistry grignard-reagent
edited Dec 8 at 12:24
Kelly Shepphard
63112
asked Dec 8 at 4:53
Ujjwal Sharma
291
3
I have never come across HMgX as a synthetic reagent, and I'm unsure of its existence. This review may offer more detail though onlinelibrary.wiley.com/doi/full/10.1002/anie.201708592
– Waylander
Dec 8 at 8:34
I’d argue that Grignards are organometallic species. HMgX is not organometallic. But at the end of the day it is semantics.
– orthocresol♦
Dec 8 at 11:36
add a comment |
up vote
5
down vote
favorite
up vote
5
down vote
favorite
We do know that the Grignard Reagent is $ce{RMgX}$ where R is some alkyl group & X is any halogen group.
So, my question is that, whether $ce{HMgX}$ is also a Grignard Reagent like $ce{RMgBr}$?
organic-chemistry grignard-reagent
edited Dec 8 at 12:24
Kelly Shepphard
63112
asked Dec 8 at 4:53
Ujjwal Sharma
291
We do know that the Grignard Reagent is $ce{RMgX}$ where R is some alkyl group & X is any halogen group.
So, my question is that, whether $ce{HMgX}$ is also a Grignard Reagent like $ce{RMgBr}$?
organic-chemistry grignard-reagent
organic-chemistry grignard-reagent
edited Dec 8 at 12:24
Kelly Shepphard
63112
asked Dec 8 at 4:53
Ujjwal Sharma
291
edited Dec 8 at 12:24
Kelly Shepphard
63112
asked Dec 8 at 4:53
Ujjwal Sharma
291
edited Dec 8 at 12:24
Kelly Shepphard
63112
edited Dec 8 at 12:24
Kelly Shepphard
63112
edited Dec 8 at 12:24
Kelly Shepphard
63112
63112
asked Dec 8 at 4:53
Ujjwal Sharma
291
asked Dec 8 at 4:53
Ujjwal Sharma
291
asked Dec 8 at 4:53
Ujjwal Sharma
291
291
3
I have never come across HMgX as a synthetic reagent, and I'm unsure of its existence. This review may offer more detail though onlinelibrary.wiley.com/doi/full/10.1002/anie.201708592
– Waylander
Dec 8 at 8:34
I’d argue that Grignards are organometallic species. HMgX is not organometallic. But at the end of the day it is semantics.
– orthocresol♦
Dec 8 at 11:36
add a comment |
3
I have never come across HMgX as a synthetic reagent, and I'm unsure of its existence. This review may offer more detail though onlinelibrary.wiley.com/doi/full/10.1002/anie.201708592
– Waylander
Dec 8 at 8:34
I’d argue that Grignards are organometallic species. HMgX is not organometallic. But at the end of the day it is semantics.
– orthocresol♦
Dec 8 at 11:36
3
3
I have never come across HMgX as a synthetic reagent, and I'm unsure of its existence. This review may offer more detail though onlinelibrary.wiley.com/doi/full/10.1002/anie.201708592
– Waylander
Dec 8 at 8:34
I have never come across HMgX as a synthetic reagent, and I'm unsure of its existence. This review may offer more detail though onlinelibrary.wiley.com/doi/full/10.1002/anie.201708592
– Waylander
Dec 8 at 8:34
I’d argue that Grignards are organometallic species. HMgX is not organometallic. But at the end of the day it is semantics.
– orthocresol♦
Dec 8 at 11:36
I’d argue that Grignards are organometallic species. HMgX is not organometallic. But at the end of the day it is semantics.
– orthocresol♦
Dec 8 at 11:36
add a comment |
1 Answer
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According to this reference $ce{HMgX}$ compounds are a thing. You can't make them with magnesium +$ce{HX}$, of course (what actually happens?), but you can get them from magnesium halide salts plus an "active" form of magnesium hydride in THF. They act as hydride ion sources for reaction with $ce{AlH3}$ and $ce{BH3}$ (forming mixed tetrahydridoaluminate and tetrahydridoborate salts, respectively), so we may reasonably expect the same sort of hydride transfer with organic substrates. Such a hydride transfer would be analogous to conventional Grignard reagents transferring their alkyl or aryl anion moieties.
answered Dec 8 at 9:46
Oscar Lanzi
14.3k12546
4
But it is probably better not to call them a Grignard reagent as they will have far more in common with metal hydrides.
– matt_black
Dec 8 at 15:39
Do we call them "Grignard reagents"? Do we call Pluto or Ceres a "planet"? That's ultimately not so much a law of nature as our nature.
– Oscar Lanzi
Dec 9 at 22:48
add a comment |
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1 Answer
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1 Answer
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active
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up vote
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According to this reference $ce{HMgX}$ compounds are a thing. You can't make them with magnesium +$ce{HX}$, of course (what actually happens?), but you can get them from magnesium halide salts plus an "active" form of magnesium hydride in THF. They act as hydride ion sources for reaction with $ce{AlH3}$ and $ce{BH3}$ (forming mixed tetrahydridoaluminate and tetrahydridoborate salts, respectively), so we may reasonably expect the same sort of hydride transfer with organic substrates. Such a hydride transfer would be analogous to conventional Grignard reagents transferring their alkyl or aryl anion moieties.
answered Dec 8 at 9:46
Oscar Lanzi
14.3k12546
4
But it is probably better not to call them a Grignard reagent as they will have far more in common with metal hydrides.
– matt_black
Dec 8 at 15:39
Do we call them "Grignard reagents"? Do we call Pluto or Ceres a "planet"? That's ultimately not so much a law of nature as our nature.
– Oscar Lanzi
Dec 9 at 22:48
add a comment |
up vote
6
down vote
According to this reference $ce{HMgX}$ compounds are a thing. You can't make them with magnesium +$ce{HX}$, of course (what actually happens?), but you can get them from magnesium halide salts plus an "active" form of magnesium hydride in THF. They act as hydride ion sources for reaction with $ce{AlH3}$ and $ce{BH3}$ (forming mixed tetrahydridoaluminate and tetrahydridoborate salts, respectively), so we may reasonably expect the same sort of hydride transfer with organic substrates. Such a hydride transfer would be analogous to conventional Grignard reagents transferring their alkyl or aryl anion moieties.
answered Dec 8 at 9:46
Oscar Lanzi
14.3k12546
4
But it is probably better not to call them a Grignard reagent as they will have far more in common with metal hydrides.
– matt_black
Dec 8 at 15:39
Do we call them "Grignard reagents"? Do we call Pluto or Ceres a "planet"? That's ultimately not so much a law of nature as our nature.
– Oscar Lanzi
Dec 9 at 22:48
add a comment |
up vote
6
down vote
up vote
6
down vote
According to this reference $ce{HMgX}$ compounds are a thing. You can't make them with magnesium +$ce{HX}$, of course (what actually happens?), but you can get them from magnesium halide salts plus an "active" form of magnesium hydride in THF. They act as hydride ion sources for reaction with $ce{AlH3}$ and $ce{BH3}$ (forming mixed tetrahydridoaluminate and tetrahydridoborate salts, respectively), so we may reasonably expect the same sort of hydride transfer with organic substrates. Such a hydride transfer would be analogous to conventional Grignard reagents transferring their alkyl or aryl anion moieties.
answered Dec 8 at 9:46
Oscar Lanzi
14.3k12546
According to this reference $ce{HMgX}$ compounds are a thing. You can't make them with magnesium +$ce{HX}$, of course (what actually happens?), but you can get them from magnesium halide salts plus an "active" form of magnesium hydride in THF. They act as hydride ion sources for reaction with $ce{AlH3}$ and $ce{BH3}$ (forming mixed tetrahydridoaluminate and tetrahydridoborate salts, respectively), so we may reasonably expect the same sort of hydride transfer with organic substrates. Such a hydride transfer would be analogous to conventional Grignard reagents transferring their alkyl or aryl anion moieties.
answered Dec 8 at 9:46
Oscar Lanzi
14.3k12546
edited Dec 8 at 12:21
answered Dec 8 at 9:46
Oscar Lanzi
14.3k12546
answered Dec 8 at 9:46
Oscar Lanzi
14.3k12546
answered Dec 8 at 9:46
Oscar Lanzi
14.3k12546
14.3k12546
4
But it is probably better not to call them a Grignard reagent as they will have far more in common with metal hydrides.
– matt_black
Dec 8 at 15:39
Do we call them "Grignard reagents"? Do we call Pluto or Ceres a "planet"? That's ultimately not so much a law of nature as our nature.
– Oscar Lanzi
Dec 9 at 22:48
add a comment |
4
But it is probably better not to call them a Grignard reagent as they will have far more in common with metal hydrides.
– matt_black
Dec 8 at 15:39
Do we call them "Grignard reagents"? Do we call Pluto or Ceres a "planet"? That's ultimately not so much a law of nature as our nature.
– Oscar Lanzi
Dec 9 at 22:48
4
4
But it is probably better not to call them a Grignard reagent as they will have far more in common with metal hydrides.
– matt_black
Dec 8 at 15:39
But it is probably better not to call them a Grignard reagent as they will have far more in common with metal hydrides.
– matt_black
Dec 8 at 15:39
Do we call them "Grignard reagents"? Do we call Pluto or Ceres a "planet"? That's ultimately not so much a law of nature as our nature.
– Oscar Lanzi
Dec 9 at 22:48
Do we call them "Grignard reagents"? Do we call Pluto or Ceres a "planet"? That's ultimately not so much a law of nature as our nature.
– Oscar Lanzi
Dec 9 at 22:48
add a comment |
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I have never come across HMgX as a synthetic reagent, and I'm unsure of its existence. This review may offer more detail though onlinelibrary.wiley.com/doi/full/10.1002/anie.201708592
– Waylander
Dec 8 at 8:34
I’d argue that Grignards are organometallic species. HMgX is not organometallic. But at the end of the day it is semantics.
– orthocresol♦
Dec 8 at 11:36