Re: ORGLIST: Imines on Everybody Digest, Vol 43, Issue 6

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From: Ilya Avrutov (IAvrutov$##$dalton.com)
Date: Wed Jan 30 2008 - 09:26:58 EST


Dear all,
 
My 2 cents to the statement:
"Have you added molecular sieves to the reaction mixture? When I made
imines from aldehydes and amines (I don't know if there are more ways)
the use of m.s. was imperative, as it is an equilibrium with the water
formed. The yield should be close to 100%. If not, try in total
anhydrous conditions."

It could be done also in the not water-mixing solvent in the presence of
solid KOH. Due to its high hygroscopicity, it bounds forming water and
forming separate aqueous alcali layer. It removes water from the
reaction environment.
 
Best,
Ilya

________________________________

From: everybody-bounces$##$orglist.net
[mailto:everybody-bounces$##$orglist.net] On Behalf Of Miguel Santos
Sent: Tuesday, January 29, 2008 4:02 PM
To: everybody$##$orglist.net
Subject: Re: ORGLIST: Imines on Everybody Digest, Vol 43, Issue 6

Hi Uno!
 
Have you added molecular sieves to the reaction mixture? When I made
imines from aldehydes and amines (I don't know if there are more ways)
the use of m.s. was imperative, as it is an equilibrium with the water
formed. The yield should be close to 100%. If not, try in total
anhydrous conditions.
 
Hope it helps.
 
Miguel

________________________________

> From: everybody-request$##$orglist.net
> Subject: Everybody Digest, Vol 43, Issue 6
> To: everybody$##$orglist.net
> Date: Mon, 28 Jan 2008 12:00:19 -0500
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> Today's Topics:
>
> 1. Re: Everybody Digest, Vol 43, Issue 5 (mahboob chem)
> 2. Re: Davis reagent (Rossana Ferrara) (abdellah yamani)
> 3. imine (Uno M?eorg)
> 4. Re: Davis reagent (Petr Melsa)
>
>
> ----------------------------------------------------------------------
>
> Message: 1
> Date: Thu, 24 Jan 2008 09:40:24 -0800 (PST)
> From: mahboob chem <mahboobchem$##$yahoo.com>
> Subject: Re: ORGLIST: Everybody Digest, Vol 43, Issue 5
> To: everybody$##$orglist.net
> Message-ID: <486287.29203.qm$##$web32402.mail.mud.yahoo.com>
> Content-Type: text/plain; charset="iso-8859-1"
>
> Dear sir and their member, i am sending paper and croos reference as
attachment
>
> Mahboob Alam
>
> Org Lett. 2005 Nov 24;7 (24):5493-5496 16288539 A New General Method
for the Preparation of N-Sulfonyloxaziridines. [My paper] Jos? Garc?a
Ruano , Jos? Alem?n , Cristina Fajardo , Alejandro Parra A simple
procedure to obtain N-alkylsulfonyl- and N-arylsulfonyloxaziridines from
the corresponding N-sulfinylimines involving a one-pot, two-step
oxidation process with m-CPBA (1 equiv) and m-CPBA/KOH (1.1 equiv) is
reported. The method is applicable to N-sulfinylimines derived from
aldehydes (aliphatic and aromatic) and ketones (dialkyl and aryl alkyl)
and preserves C=C-conjugated double bonds. Almost quantitative yields,
very mild conditions (usually less than 5 min at room temperature), and
easy purification by filtration are the main features of this new
procedure, which can be performed at a gram scale.
>
>
>
>
>
> everybody-request$##$orglist.net wrote: Send Everybody mailing list
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> 1. Davis reagent (Rossana Ferrara)
>
>
> ----------------------------------------------------------------------
>
> Message: 1
> Date: Thu, 24 Jan 2008 11:07:33 +0100
> From: Rossana Ferrara
> Subject: ORGLIST: Davis reagent
> To: everybody$##$orglist.net
> Message-ID:
> Content-Type: text/plain; charset="us-ascii"
>
> Dear all,
> I'd like to know some information about davis reagent
(N-sulfonyloxaziridines): is it possible to buy it?Do you know the
procedure to make it?Can you give me some references about?
> Thanks a lot for you help
> Kind regards
> Rossana Ferrara
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> ------------------------------
>
> Message: 2
> Date: Thu, 24 Jan 2008 09:52:39 -0800 (PST)
> From: abdellah yamani <abyamani_72$##$yahoo.com>
> Subject: Re: ORGLIST: Davis reagent (Rossana Ferrara)
> To: everybody$##$orglist.net
> Message-ID: <303747.7598.qm$##$web56101.mail.re3.yahoo.com>
> Content-Type: text/plain; charset="us-ascii"
>
> Dear,
> Please find the reference regarding general method for the preparation
of N-sulfonyloxaziridines.
>
> Org Lett. 2005 Nov 24;7 (24):5493-5496 16288539
>
> Good luck,
>
>
> Abdellah Yamani
>
>
>
> ----- Original Message ----
> From: "everybody-request$##$orglist.net" <everybody-request$##$orglist.net>
> To: everybody$##$orglist.net
> Sent: Thursday, January 24, 2008 6:01:01 PM
> Subject: Everybody Digest, Vol 43, Issue 5
>
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> Today's Topics:
>
> 1. Davis reagent (Rossana Ferrara)
>
>
> ----------------------------------------------------------------------
>
> Message: 1
> Date: Thu, 24 Jan 2008 11:07:33 +0100
> From: Rossana Ferrara <rossana.ferrara$##$unimi.it>
> Subject: ORGLIST: Davis reagent
> To: everybody$##$orglist.net
> Message-ID: <f70dd9d315455.47987175$##$unimi.it>
> Content-Type: text/plain; charset="us-ascii"
>
> Dear all,
> I'd like to know some information about davis reagent
(N-sulfonyloxaziridines): is it possible to buy it?Do you know the
procedure to make it?Can you give me some references about?
> Thanks a lot for you help
> Kind regards
> Rossana Ferrara
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> Message: 3
> Date: Fri, 25 Jan 2008 00:47:04 +0200
> From: Uno M?eorg <uno$##$chem.ut.ee>
> Subject: ORGLIST: imine
> To: everybody$##$lists2.orglist.net
> Message-ID: <20080124224702.E71DF29F7F5$##$Relayhost1.neti.ee>
> Content-Type: text/plain; charset="us-ascii"; format=flowed
>
> Hi colleagues,
>
> I had to play recently with simple chemistry: the synthesis of
> methylenimine of 2,6-dimethylaniline.
>
> To my big surprise there are only six references about preparation of
> this compound.
>
> There are two patents where are quite well described procedures: the
> substituted aniline pluss, 1,3,5-trioxane in heptane. Nothing happend
> by heating within several hrs. After addition of triethyl amine
> methanol solution ( as it was used in other samples in this patent)
> again nothing happend.
>
> Then in Chem. Commm paper similars synthesis is mentioned where
> 2,6-diisopropyl aniline was used as starting material and the
> reaction was performed with paraform under heating without solvent.
> There is not given normal description of procedure. When we tried
> this method only black tar was obtained after distillation of the
> non-reacted aniline.
>
>
> Have somebody any experience with this compound. I will be very happy
> about your help, comments recommendations, suggestions.
>
>
> Regards
>
> Uno
>
>
>
>
>
>
> ------------------------------
>
> Message: 4
> Date: Sat, 26 Jan 2008 07:42:04 +0100
> From: "Petr Melsa" <melsap$##$gmail.com>
> Subject: Re: ORGLIST: Davis reagent
> To: "Rossana Ferrara" <rossana.ferrara$##$unimi.it>
> Cc: everybody$##$orglist.net
> Message-ID:
> <b4ade9ff0801252242r315003fdn145a6e7f54506506$##$mail.gmail.com>
> Content-Type: text/plain; charset="iso-8859-1"
>
> Dear Rossana,
>
> the procedure is available on www.orgsyn.org
>
http://orgsyn.org/orgsyn/default.asp?formgroup=basenpe_form_group&dataac
tion=db&dbname=orgsyn
>
> Petr
>
> On Jan 24, 2008 11:07 AM, Rossana Ferrara <rossana.ferrara$##$unimi.it>
wrote:
>
> > Dear all,
> > I'd like to know some information about davis reagent
> > (N-sulfonyloxaziridines): is it possible to buy it?Do you know the
procedure
> > to make it?Can you give me some references about?
> > Thanks a lot for you help
> > Kind regards
> > Rossana Ferrara
> >
> > _______________________________________________
> > ORGLIST - Organic Chemistry Mailing List
> > Website / Archive / FAQ: http://www.orglist.net
> > To post a message (TO EVERYBODY) send to everybody$##$orglist.net
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>
>
>
> --
> PM
>
> Chinese saying: It is difficult to find a black cat in a dark room,
> especially if there is no cat.
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