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Lossen Rearrangement Mechanism Overview

The document discusses the Lossen rearrangement, an intramolecular reaction converting hydroxamic acids into isocyanates, which can further be transformed into primary amines. It outlines the mechanism in six steps, including proton abstraction, group migration, hydrolysis, and decarboxylation. The document is authored by S. R. Mohamed Vaseem from Sadakathullah Appa College, which is reaccredited with an 'A++' grade by NAAC.

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260 views6 pages

Lossen Rearrangement Mechanism Overview

The document discusses the Lossen rearrangement, an intramolecular reaction converting hydroxamic acids into isocyanates, which can further be transformed into primary amines. It outlines the mechanism in six steps, including proton abstraction, group migration, hydrolysis, and decarboxylation. The document is authored by S. R. Mohamed Vaseem from Sadakathullah Appa College, which is reaccredited with an 'A++' grade by NAAC.

Uploaded by

Rasik
Copyright
© All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PPTX, PDF, TXT or read online on Scribd

Sadakathullah Appa College (Autonomous)

Reaccredited by NAAC at an 'A++' Grade with a CGPA of 3.56


ISO 9001: 2015 Certified Institution
Rahmath Nagar, Tirunelveli - 627 011.

ORGANIC REACTION MACHANISM-II

TOPIC: LOSSEN REARRANGEMENT

BY,
S. R. MOHAMED VASEEM
24SCH18
I [Link]. CHEMISTRY

1
Lossen Rearrangement

• The Lossen rearrangement is the intramolecular conversion of hydroxamic acids or their

O-acetyl, O-aroyl, and O-sulfonyl derivatives into isocyanates under thermal or in the

presence of acid or base catalysts.

• Isocyanate can be converted to the corresponding primary amine with water.


MECHANISM STEPS

Step 1: Abstraction of the proton from the N atom.

Step 2: Migration of R1 group to the N-atom and elimination of


carboxylate.

Step 3: Hydrolysis of isocyanate and nucleophilic attack by water.

Step 4: Proton transfer.

Step 5: Decarboxylation and liberation of carbon dioxide.

Step 6: Proton transfer and formation of an amine product


MECHANISM
APPLICATION

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