From: Sengen Sun (sengensun$##$yahoo.com)
Date: Thu May 04 2006 - 18:17:11 EDT
What I did on a secondary alcohol was:
1. to react with TfOTf to make triflate ester.
2. to treat the ester with BzSNa in DMF at 80 oC in
DMF for 5h.
3. to treat the resulting thiobenzoyl ester with MeONa
to remove the benzoyl group.
These steps lead to reversion of the configuration at
the reaction center. I did these reactions on a ribose
ring, and had them published in RNA 1997, 3:1352-1363.
Sengen
--- Guido de Silvestri <guidods$##$etb.net.co> wrote:
>
> Dear Madhav...
>
> This kind of processes has to be carrying about
> within two stages:
>
> As a first step, a synthesis of an alkylhalide from
> the alcohol can be
> possible using thionyl chloride:
>
> ROH +SOCL2 = RCl+SO2 +HCl
>
> Here, pyridine is used as an alkaline absorption
> agent, yielding the HCl
> to pyridine chloride
>
> In a second stage, the alkyl halide (that it is easy
> to separate from
> the reaction mixture), could react with a metallic
> hydrosulfide making a
> nucleophylic substitution, into an alcoholic
> solution:
>
> RCl + NaSH = RSH + NaCl
>
> In addition, this process is very useful to the
> primaries merchaptans
> synthesis, but not when a secondary or a tertiary
> halide is involved,
> because those could be easy deydrogenalized in
> presence of strong bases.
>
> Best regards,
>
> Guido de Silvestri
> Process Engineer
>
>
>
>
>
> -----Mensaje original-----
> De: everybody-bounces$##$orglist.net
> [mailto:everybody-bounces$##$orglist.net]
> En nombre de madhav mallia
> Enviado el: Miércoles, 03 de Mayo de 2006 06:16 a.m.
> Para: everybody$##$orglist.net
> Asunto: ORGLIST: conversion of OH group to SH
>
> i want to convert aliphatic alcohol to thiol. what
> are
> the options available? help needed.
>
> thanks in advance
>
> madhav
>
>
>
>
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