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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: simonraj on April 06, 2012, 02:03:58 AM

Title: conversion of aliphatic terminal alkyl chains to azide
Post by: simonraj on April 06, 2012, 02:03:58 AM

Dear members,

I would like to know how to convert aliphatic terminal alkyl chain to azide (N3).


Thanks in advance

Simonraj
Title: Re: conversion of aliphatic terminal alkyl chains to azide
Post by: discodermolide on April 06, 2012, 02:19:08 AM
Quote from: simonraj on April 06, 2012, 02:03:58 AM

Dear members,

I would like to know how to convert aliphatic terminal alkyl chain to azide (N3).


Thanks in advance

Simonraj

Have you any ideas?
Title: Re: conversion of aliphatic terminal alkyl chains to azide
Post by: simonraj on April 06, 2012, 02:48:38 AM
Quote from: discodermolide on April 06, 2012, 02:19:08 AM
Quote from: simonraj on April 06, 2012, 02:03:58 AM

Dear members,

I would like to know how to convert aliphatic terminal alkyl chain to azide (N3).


Thanks in advance

Simonraj

Have you any ideas?

(i) bromination/chlorination  (ii) Aq. Sodium azide  -----> Alkyl azide

Title: Re: conversion of aliphatic terminal alkyl chains to azide
Post by: discodermolide on April 06, 2012, 03:05:20 AM
Quote from: simonraj on April 06, 2012, 02:48:38 AM
Quote from: discodermolide on April 06, 2012, 02:19:08 AM
Quote from: simonraj on April 06, 2012, 02:03:58 AM

Dear members,

I would like to know how to convert aliphatic terminal alkyl chain to azide (N3).


Thanks in advance

Simonraj




Have you any ideas?

(i) bromination/chlorination  (ii) Aq. Sodium azide  -----> Alkyl azide



That would give you some product along with a host of others because halogenation does not just occur at the chain terminus.
Title: Re: conversion of aliphatic terminal alkyl chains to azide
Post by: simonraj on April 06, 2012, 03:13:04 AM
Then is it possible to convert terminal alkyl chains to terminal alkyne chains?

Quote from: discodermolide on April 06, 2012, 03:05:20 AM
Quote from: simonraj on April 06, 2012, 02:48:38 AM
Quote from: discodermolide on April 06, 2012, 02:19:08 AM
Quote from: simonraj on April 06, 2012, 02:03:58 AM

Dear members,

I would like to know how to convert aliphatic terminal alkyl chain to azide (N3).


Thanks in advance

Simonraj




Have you any ideas?

(i) bromination/chlorination  (ii) Aq. Sodium azide  -----> Alkyl azide



That would give you some product along with a host of others because halogenation does not just occur at the chain terminus.
Title: Re: conversion of aliphatic terminal alkyl chains to azide
Post by: discodermolide on April 06, 2012, 03:16:55 AM
Same problem
Title: Re: conversion of aliphatic terminal alkyl chains to azide
Post by: simonraj on April 06, 2012, 03:28:59 AM
Ok,

how to convert dodecane to 1-dodecanamine?
Title: Re: conversion of aliphatic terminal alkyl chains to azide
Post by: discodermolide on April 06, 2012, 03:37:01 AM
Quote from: simonraj on April 06, 2012, 03:28:59 AM
Ok,

how to convert dodecane to 1-dodecanamine?


Same problem, any sort of radical halogenation will give a mixture of products, the terminal product in the minority.
Title: Re: conversion of aliphatic terminal alkyl chains to azide
Post by: simonraj on April 06, 2012, 04:03:03 AM

But, I just found one reference to prepare 1-dodecanamine:  Chemistry Letters, 6, p. 635, 1977
 whis is not avalible as a soft copy from the journal.
Title: Re: conversion of aliphatic terminal alkyl chains to azide
Post by: AWK on April 06, 2012, 04:35:35 AM
But this reference use alcohols not hydrocarbons.

http://www.journalarchive.jst.go.jp/english/jnlabstract_en.php?cdjournal=cl1972&cdvol=6&noissue=6&startpage=635
Title: Re: conversion of aliphatic terminal alkyl chains to azide
Post by: simonraj on April 06, 2012, 05:06:10 AM
Yes your right. Thanks.

Then, you please tell me how to convert dodecane to 1-dodecanol.
Title: Re: conversion of aliphatic terminal alkyl chains to azide
Post by: simonraj on April 06, 2012, 05:19:12 AM

Plese tell me

Is this possible ?
R-(CH2)n-CH3    Chlorine, TEL and Temp: 1400C------>   R-(CH2)n-CH2-Cl


Title: Re: conversion of aliphatic terminal alkyl chains to azide
Post by: discodermolide on April 06, 2012, 05:24:09 AM
Quote from: simonraj on April 06, 2012, 05:19:12 AM

Plese tell me

Is this possible ?
R-(CH2)n-CH3    Chlorine, TEL and Temp: 1400C------>   R-(CH2)n-CH2-Cl





What is TEL?
As I said you will get terminal chlorination but it will be a MINOR product.
Title: Re: conversion of aliphatic terminal alkyl chains to azide
Post by: simonraj on April 06, 2012, 05:26:53 AM
TEL: Tetraethyllead


Quote from: discodermolide on April 06, 2012, 05:24:09 AM
Quote from: simonraj on April 06, 2012, 05:19:12 AM

Plese tell me

Is this possible ?
R-(CH2)n-CH3    Chlorine, TEL and Temp: 1400C------>   R-(CH2)n-CH2-Cl





What is TEL?
As I said you will get terminal chlorination but it will be a MINOR product.

Title: Re: conversion of aliphatic terminal alkyl chains to azide
Post by: discodermolide on April 06, 2012, 05:34:55 AM
I have now idea if it will work. But I do not advise the use of tetraethyl lead, which is an extremely toxic substance.
Anyway the higher the temperature the greater the chance of side reactions.

Title: Re: conversion of aliphatic terminal alkyl chains to azide
Post by: simonraj on April 06, 2012, 05:39:56 AM
OK, thank you.

An alternative to TEL is Methyl Tertiary Butyl Ether.


Quote from: discodermolide on April 06, 2012, 05:34:55 AM
I have now idea if it will work. But I do not advise the use of tetraethyl lead, which is an extremely toxic substance.
Anyway the higher the temperature the greater the chance of side reactions.


Title: Re: conversion of aliphatic terminal alkyl chains to azide
Post by: discodermolide on April 06, 2012, 05:45:25 AM
Quote from: simonraj on April 06, 2012, 05:39:56 AM
OK, thank you.

An alternative to TEL is Methyl Tertiary Butyl Ether.


Quote from: discodermolide on April 06, 2012, 05:34:55 AM
I have now idea if it will work. But I do not advise the use of tetraethyl lead, which is an extremely toxic substance.
Anyway the higher the temperature the greater the chance of side reactions.




I fail to see how MTBE can be an alternative to tetraethyl lead!!!!!
As I said many times before you will get a mixture using these conditions.

Can you not utilize two starting materials and couple them?
Title: Re: conversion of aliphatic terminal alkyl chains to azide
Post by: AWK on April 06, 2012, 11:22:59 AM
http://www.patentgenius.com/patent/3948741.html
Title: Re: conversion of aliphatic terminal alkyl chains to azide
Post by: orgopete on April 07, 2012, 03:19:32 AM
Why not start with an alpha olefin, like 1-dodecene?
http://en.wikipedia.org/wiki/Linear_alpha_olefin