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orthocresol
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enter image description hereRearrangements in Clemmensen reduction

What is the possible mechanism for this reaction? Activated zinc in presence of concentrated hydrochloric acid is used for Clemmensen reduction, that is conversion of ketone group to methylene group.

  I'd expect the product to be 1-methyl-2-propyl-pyrrolidine.propylpyrrolidine:

1-methyl-2-propylpyrrolidine

However, ring expansion occurs leading to a piperidine derivative. Could anyone please explain or provide a mechanism for the conversion? Thanks!

enter image description here

What is the possible mechanism for this reaction? Activated zinc in presence of concentrated hydrochloric acid is used for Clemmensen reduction, that is conversion of ketone group to methylene group.

  I'd expect the product to be 1-methyl-2-propyl-pyrrolidine. However, ring expansion occurs leading to a piperidine derivative. Could anyone please explain or provide a mechanism for the conversion? Thanks!

Rearrangements in Clemmensen reduction

What is the possible mechanism for this reaction? Activated zinc in presence of concentrated hydrochloric acid is used for Clemmensen reduction, that is conversion of ketone group to methylene group. I'd expect the product to be 1-methyl-2-propylpyrrolidine:

1-methyl-2-propylpyrrolidine

However, ring expansion occurs leading to a piperidine derivative. Could anyone please explain or provide a mechanism for the conversion? Thanks!

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orthocresol
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Reduction with Ring Expansion Rearrangements of α-aminoketones in Clemmensen reduction

enter image description here

What is the possible mechanism for this reaction? Activated zinc in presence of concentrated hydrochloric acid is used for Clemmensen reduction, that is conversion of ketone group to methylene group.

I'd expect the product to be 1-methyl 2-2-propyl pyrroidine-pyrrolidine. However, however ring expansion occurs leading to a piperidine derivative. Could anyone please explain or provide a mechanism for the conversion? Thanks!

Reduction with Ring Expansion

enter image description here

What is the possible mechanism for this reaction? Activated zinc in presence of concentrated hydrochloric acid is used for Clemmensen reduction, that is conversion of ketone group to methylene group

I'd expect the product to be 1-methyl 2-propyl pyrroidine, however ring expansion occurs leading to a piperidine derivative. Could anyone please explain or provide a mechanism for the conversion? Thanks!

Rearrangements of α-aminoketones in Clemmensen reduction

enter image description here

What is the possible mechanism for this reaction? Activated zinc in presence of concentrated hydrochloric acid is used for Clemmensen reduction, that is conversion of ketone group to methylene group.

I'd expect the product to be 1-methyl-2-propyl-pyrrolidine. However, ring expansion occurs leading to a piperidine derivative. Could anyone please explain or provide a mechanism for the conversion? Thanks!

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stoic-santiago
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Reduction with Ring Expansion

enter image description here

What is the possible mechanism for this reaction? Activated zinc in presence of concentrated hydrochloric acid is used for Clemmensen reduction, that is conversion of ketone group to methylene group

I'd expect the product to be 1-methyl 2-propyl pyrroidine, however ring expansion occurs leading to a piperidine derivative. Could anyone please explain or provide a mechanism for the conversion? Thanks!