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Grignard reagent with sulfur dioxide

Amide synthesis SM alkylchlorideSN2 with thionyl chloridesThe reactions of grignard reagentPreparation of an aromatic Grignard reagentDoes grignard reagent react with oxygen?Reaction of Grignard reagent with primary aminesGrignard reagent and acidic hydrogen

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2

$begingroup$

I have studied that the Grignard reagent $ceRMgX$ reacts with $ceCO2$ to form $ceRCOOH$ after acid hydrolysis. But does the same apply for sulfur dioxide?

Grignard reagents are good bases and also good nucleophiles.
So the alkyl anion will attack the electron deficient carbon atom in $ceCO2.$

But in the case of $ceSO2$ the following conditions aren't present.
First of all, sulfur is more electronegative than carbon. Secondly, sulfur has a lone pair of electrons which the carbon lacks. So this should further discourage an attack by the Grignard's alkyl anion.

So, what actually will happen when Grignards are treated with $ceSO2?$

organic-chemistry grignard-reagent

share|improve this question

edited 8 hours ago

andselisk♦

22.4k88 gold badges7878 silver badges149149 bronze badges

asked 11 hours ago

Dheeraj KamathDheeraj Kamath

3177 bronze badges

$endgroup$

• 
  
  
  

  
  1
  

  
  
  
  
  
  

  
  $begingroup$
  I'm pretty sure they will react.
  $endgroup$
  – Ivan Neretin
  10 hours ago
  

  
  
  
  


• 
  
  
  

  
  

  
  
  
  
  
  

  
  $begingroup$
  A Grignard reagent is basically (pun intended) a bull in a china shop. It will go after just about anything having a hint of Bronsted or Lewis acidity.
  $endgroup$
  – Oscar Lanzi
  4 hours ago
  

  
  
  
  

add a comment
 | 

2

$begingroup$

I have studied that the Grignard reagent $ceRMgX$ reacts with $ceCO2$ to form $ceRCOOH$ after acid hydrolysis. But does the same apply for sulfur dioxide?

Grignard reagents are good bases and also good nucleophiles.
So the alkyl anion will attack the electron deficient carbon atom in $ceCO2.$

But in the case of $ceSO2$ the following conditions aren't present.
First of all, sulfur is more electronegative than carbon. Secondly, sulfur has a lone pair of electrons which the carbon lacks. So this should further discourage an attack by the Grignard's alkyl anion.

So, what actually will happen when Grignards are treated with $ceSO2?$

organic-chemistry grignard-reagent

share|improve this question

edited 8 hours ago

andselisk♦

22.4k88 gold badges7878 silver badges149149 bronze badges

asked 11 hours ago

Dheeraj KamathDheeraj Kamath

3177 bronze badges

$endgroup$

• 
  
  
  

  
  1
  

  
  
  
  
  
  

  
  $begingroup$
  I'm pretty sure they will react.
  $endgroup$
  – Ivan Neretin
  10 hours ago
  

  
  
  
  


• 
  
  
  

  
  

  
  
  
  
  
  

  
  $begingroup$
  A Grignard reagent is basically (pun intended) a bull in a china shop. It will go after just about anything having a hint of Bronsted or Lewis acidity.
  $endgroup$
  – Oscar Lanzi
  4 hours ago
  

  
  
  
  

add a comment
 | 

$begingroup$

I have studied that the Grignard reagent $ceRMgX$ reacts with $ceCO2$ to form $ceRCOOH$ after acid hydrolysis. But does the same apply for sulfur dioxide?

Grignard reagents are good bases and also good nucleophiles.
So the alkyl anion will attack the electron deficient carbon atom in $ceCO2.$

But in the case of $ceSO2$ the following conditions aren't present.
First of all, sulfur is more electronegative than carbon. Secondly, sulfur has a lone pair of electrons which the carbon lacks. So this should further discourage an attack by the Grignard's alkyl anion.

So, what actually will happen when Grignards are treated with $ceSO2?$

organic-chemistry grignard-reagent

share|improve this question

edited 8 hours ago

andselisk♦

22.4k88 gold badges7878 silver badges149149 bronze badges

asked 11 hours ago

Dheeraj KamathDheeraj Kamath

3177 bronze badges

$endgroup$

share|improve this question

edited 8 hours ago

andselisk♦

22.4k88 gold badges7878 silver badges149149 bronze badges

asked 11 hours ago

Dheeraj KamathDheeraj Kamath

3177 bronze badges

share|improve this question

edited 8 hours ago

andselisk♦

22.4k88 gold badges7878 silver badges149149 bronze badges

asked 11 hours ago

Dheeraj KamathDheeraj Kamath

3177 bronze badges

edited 8 hours ago

andselisk♦

22.4k88 gold badges7878 silver badges149149 bronze badges

edited 8 hours ago

andselisk♦

22.4k88 gold badges7878 silver badges149149 bronze badges

asked 11 hours ago

Dheeraj KamathDheeraj Kamath

3177 bronze badges

asked 11 hours ago

Dheeraj KamathDheeraj Kamath

3177 bronze badges

1 Answer
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5

$begingroup$

You get sulfinic acids $ceRSO2H.$

This paper by Dowson et al. [1] states that Grignard plus $ceSO2$ gives sulfinic acids and as a reference quotes an older article by Allen Jr. et al. [2] which states

The reaction between sulfur dioxide and Grignard reagent has been widely used for the preparation of aromatic and aliphatic sulfinic acids.

I would suggest you read [2] and the references it quotes.

References

1. Dowson, G. R. M.; Dimitriou, I.; Owen, R. E.; Reed, D. G.; Allen, R. W. K.; Styring, P. Kinetic and Economic Analysis of Reactive Capture of Dilute Carbon Dioxide with Grignard Reagents. Faraday Discuss. 2015, 183, 47–65. https://doi.org/10/gf9hvn. (Research Gate — PDF)


2. Allen, Jr., Paul.; Rehl, W. Richard.; Fuchs, P. E. Sulfone Formation during Sulfination of the Alkyl Grignard Reagent. J. Org. Chem. 1955, 20 (9), 1237–1239. https://doi.org/10/d42z3x.

share|improve this answer

edited 8 hours ago

andselisk♦

22.4k88 gold badges7878 silver badges149149 bronze badges

answered 10 hours ago

WaylanderWaylander

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$endgroup$

add a comment
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5

$begingroup$

You get sulfinic acids $ceRSO2H.$

This paper by Dowson et al. [1] states that Grignard plus $ceSO2$ gives sulfinic acids and as a reference quotes an older article by Allen Jr. et al. [2] which states

The reaction between sulfur dioxide and Grignard reagent has been widely used for the preparation of aromatic and aliphatic sulfinic acids.

I would suggest you read [2] and the references it quotes.

References

1. Dowson, G. R. M.; Dimitriou, I.; Owen, R. E.; Reed, D. G.; Allen, R. W. K.; Styring, P. Kinetic and Economic Analysis of Reactive Capture of Dilute Carbon Dioxide with Grignard Reagents. Faraday Discuss. 2015, 183, 47–65. https://doi.org/10/gf9hvn. (Research Gate — PDF)


2. Allen, Jr., Paul.; Rehl, W. Richard.; Fuchs, P. E. Sulfone Formation during Sulfination of the Alkyl Grignard Reagent. J. Org. Chem. 1955, 20 (9), 1237–1239. https://doi.org/10/d42z3x.

share|improve this answer

edited 8 hours ago

andselisk♦

22.4k88 gold badges7878 silver badges149149 bronze badges

answered 10 hours ago

WaylanderWaylander

8,60411 gold badge1818 silver badges2929 bronze badges

$endgroup$

add a comment
 | 

5

$begingroup$

You get sulfinic acids $ceRSO2H.$

This paper by Dowson et al. [1] states that Grignard plus $ceSO2$ gives sulfinic acids and as a reference quotes an older article by Allen Jr. et al. [2] which states

The reaction between sulfur dioxide and Grignard reagent has been widely used for the preparation of aromatic and aliphatic sulfinic acids.

I would suggest you read [2] and the references it quotes.

References

1. Dowson, G. R. M.; Dimitriou, I.; Owen, R. E.; Reed, D. G.; Allen, R. W. K.; Styring, P. Kinetic and Economic Analysis of Reactive Capture of Dilute Carbon Dioxide with Grignard Reagents. Faraday Discuss. 2015, 183, 47–65. https://doi.org/10/gf9hvn. (Research Gate — PDF)


2. Allen, Jr., Paul.; Rehl, W. Richard.; Fuchs, P. E. Sulfone Formation during Sulfination of the Alkyl Grignard Reagent. J. Org. Chem. 1955, 20 (9), 1237–1239. https://doi.org/10/d42z3x.

share|improve this answer

edited 8 hours ago

andselisk♦

22.4k88 gold badges7878 silver badges149149 bronze badges

answered 10 hours ago

WaylanderWaylander

8,60411 gold badge1818 silver badges2929 bronze badges

$endgroup$

add a comment
 | 

$begingroup$

You get sulfinic acids $ceRSO2H.$

This paper by Dowson et al. [1] states that Grignard plus $ceSO2$ gives sulfinic acids and as a reference quotes an older article by Allen Jr. et al. [2] which states

The reaction between sulfur dioxide and Grignard reagent has been widely used for the preparation of aromatic and aliphatic sulfinic acids.

I would suggest you read [2] and the references it quotes.

References

1. Dowson, G. R. M.; Dimitriou, I.; Owen, R. E.; Reed, D. G.; Allen, R. W. K.; Styring, P. Kinetic and Economic Analysis of Reactive Capture of Dilute Carbon Dioxide with Grignard Reagents. Faraday Discuss. 2015, 183, 47–65. https://doi.org/10/gf9hvn. (Research Gate — PDF)


2. Allen, Jr., Paul.; Rehl, W. Richard.; Fuchs, P. E. Sulfone Formation during Sulfination of the Alkyl Grignard Reagent. J. Org. Chem. 1955, 20 (9), 1237–1239. https://doi.org/10/d42z3x.

share|improve this answer

edited 8 hours ago

andselisk♦

22.4k88 gold badges7878 silver badges149149 bronze badges

answered 10 hours ago

WaylanderWaylander

8,60411 gold badge1818 silver badges2929 bronze badges

$endgroup$

share|improve this answer

edited 8 hours ago

andselisk♦

22.4k88 gold badges7878 silver badges149149 bronze badges

answered 10 hours ago

WaylanderWaylander

8,60411 gold badge1818 silver badges2929 bronze badges

edited 8 hours ago

andselisk♦

22.4k88 gold badges7878 silver badges149149 bronze badges

edited 8 hours ago

andselisk♦

22.4k88 gold badges7878 silver badges149149 bronze badges

answered 10 hours ago

WaylanderWaylander

8,60411 gold badge1818 silver badges2929 bronze badges

answered 10 hours ago

WaylanderWaylander

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