Olefine from amine - how to make?

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Discussion Overview

The discussion revolves around the synthesis of olefins from primary amines, specifically focusing on the conversion of C16 and C18 primary amines to their respective olefins. Participants explore various chemical reactions and methods, including deamination and Hofmann elimination, while addressing the challenges associated with isomer formation and the suitability of certain reactions for aliphatic sulfonates.

Discussion Character

  • Exploratory
  • Technical explanation
  • Debate/contested

Main Points Raised

  • One participant inquires about methods to convert primary amines to olefins, noting the complexity of obtaining a single product due to potential isomer formation during deamination.
  • Another participant suggests looking into Hofmann elimination as a possible method for the conversion of RCH2CH2NH2 to RCH=CH2.
  • A participant expresses interest in the conditions necessary for performing Hofmann elimination and seeks references for proper experimental setups.
  • There is a mention of hexadecylsulfonate and a question about the applicability of desulfonation via hydrolysis for aliphatic sulfonates, drawing a comparison to previously described methods for aromatic sulfonates.

Areas of Agreement / Disagreement

Participants do not reach a consensus on the best method for synthesizing olefins from primary amines, and multiple competing views and methods are presented without resolution.

Contextual Notes

The discussion highlights uncertainties regarding the effectiveness of various reactions and the conditions required for successful implementation, particularly in the context of aliphatic versus aromatic compounds.

Helene87
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Hello! Can you please help me in my difficult situation. I ve already read much but found nothing.
So, I have primary amine (C16 and C18). I have to get the respective olefine. I watched the reaction deamination, but i ve read that it is impossible to get one product (one alcohol) from this reaction - because many isomer are appeared. If there are other way to deliver amine from amine group??
And then i have hexadecylsulfonate. Can i transfer this compound to olefine. I ve read that alkylsulfonate can be desulfonate by hydrolisis with RH as product. But it was describe for aromatic sulfonate. If this is suitable for aliphatic sulfonate?
Thank you for all help and hints. I m not organic but now i need olefine for my inorganic synthesis...
 
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sjb-2812, thank you for help.
I ve read about this elimination, i have question - Have you done such reactions? Where can i get proper conditions for its realization?
Thank you.
 
Helene87 said:
sjb-2812, thank you for help.
I ve read about this elimination, i have question - Have you done such reactions? Where can i get proper conditions for its realization?
Thank you.

I have not carried out the reaction, but there are a number of references at e.g. http://orgchem.chem.uconn.edu/namereact/hofmannelim.html or similar
 
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