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aircraftvip

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¡ï ¡ï ¡ï ¡ï ¡ï
ºìÖÛÁ÷ÐÇ: ½ð±Ò+1, Ó¦ÖúÖ¸Êý+1, ר¼Ò¿¼ºË, ˵ûÓÐÏÔÖøÑõ»¯£¬µ«ÊÇDMSO¶ÔÓÚÑõ»¯Ô­ÀíÓÖÊÇʲô£¿@liuanan 2012-08-28 09:23:26
yuzaifei: ½ð±Ò+4, Èç´ËѧÊõ£¬ËäÈ»²»ÊǺÜÓÐÓã¬Ò²¹ÄÀøÒ»Ï 2012-08-28 22:16:05
ÒýÓûØÌû:
3Â¥: Originally posted by liuanan at 2012-08-27 16:42:44
ÎÒ¾õµÃ²»ÐУ¬ÎҼǵÃDMSO¶ÔÛÏ»ùÓÐÑõ»¯×÷Ó㬹Èë׸ÊëļÓÈëÖ®ºó×Ô¼º¾Í»á±»Ñõ»¯Éú³É¶þÁò¼üÁ˰É

One original paper was J. Org. Chem., 41(11), 2061 - 2064 (1976).

It says the oxidation process worked in the presence small amount of bromine or Hydrogen bromide as catalyst, at high temperature as 180¡ãC, in the presence of water.

"Further, Lipton and Bodwel14 have reported that cystine is oxidized to cysteic  acid  by  minor  amounts  of  MezSO  under  conditions
used for the acid-catalyzed hydrolysis of proteins."

I still think the best way is to make a conclusion after practical evidence. Since nobody could tell whether the oxidation would be significant if some of the conditions (temperature, pH, catalyst...) were changed.
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4Â¥2012-08-28 03:09:43
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aircraftvip

ר¼Ò¹ËÎÊ (ÕýʽдÊÖ)

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¡ï ¡ï ¡ï
¸Ðл²ÎÓ룬ӦÖúÖ¸Êý +1
ºìÖÛÁ÷ÐÇ: ½ð±Ò+1, ר¼Ò¿¼ºË, ¸Ðл½»Á÷»ØÌû£¬µ«ÊǶþ¡¢ÈýÂ¥ÄãÁ½Ë­¶ÔË­´íÎҾͲ»ÖªµÀÁË 2012-08-27 20:33:49
yuzaifei: ½ð±Ò+2, ¡ïÓаïÖú, лл²ÎÓë 2012-08-28 22:15:08
The best way is to make a model reaction.
Of course make the reaction using DMSO-D6 as solvent in a NMR tube.
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2Â¥2012-08-27 16:24:31
ÒÑÔÄ   »Ø¸´´ËÂ¥   ¹Ø×¢TA ¸øTA·¢ÏûÏ¢ ËÍTAºì»¨ TAµÄ»ØÌû

liuanan

ר¼Ò¹ËÎÊ (ÖøÃûдÊÖ)

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¡ï ¡ï ¡ï
¸Ðл²ÎÓ룬ӦÖúÖ¸Êý +1
ºìÖÛÁ÷ÐÇ: ½ð±Ò+1, ר¼Ò¿¼ºË, ¸Ðл½»Á÷»ØÌû£¬µ«ÊǶþ¡¢ÈýÂ¥ÄãÁ½Ë­¶ÔË­´íÎҾͲ»ÖªµÀÁË 2012-08-27 20:34:00
yuzaifei: ½ð±Ò+2, ¡ïÓаïÖú, лл£¬Ò²ÌṩÁËÒ»ÖÖ¿ÉÄÜÐÔ 2012-08-28 22:15:36
ÎÒ¾õµÃ²»ÐУ¬ÎҼǵÃDMSO¶ÔÛÏ»ùÓÐÑõ»¯×÷Ó㬹Èë׸ÊëļÓÈëÖ®ºó×Ô¼º¾Í»á±»Ñõ»¯Éú³É¶þÁò¼üÁ˰É
3Â¥2012-08-27 16:42:44
ÒÑÔÄ   »Ø¸´´ËÂ¥   ¹Ø×¢TA ¸øTA·¢ÏûÏ¢ ËÍTAºì»¨ TAµÄ»ØÌû

aircraftvip

ר¼Ò¹ËÎÊ (ÕýʽдÊÖ)

¡¾´ð°¸¡¿Ó¦Öú»ØÌû

¡ï ¡ï ¡ï ¡ï ¡ï
markar: ½ð±Ò+1, ¸Ðл»ØÌû½»Á÷ 2012-08-28 15:33:44
yuzaifei: ½ð±Ò+4, ¡ïÓаïÖú, ÔÞѧÊõ£¬¸ÐлÄúµÄÈÏÕæ½²½â 2012-08-28 22:16:42
ÒýÓûØÌû:
4Â¥: Originally posted by aircraftvip at 2012-08-28 03:09:43
One original paper was J. Org. Chem., 41(11), 2061 - 2064 (1976).

It says the oxidation process worked in the presence small amount of bromine or Hydrogen bromide as catalyst, at high temperature ...

mechanism of Swern Oxidation---Wikipedia

The first step of the Swern oxidation is the low-temperature reaction of dimethyl sulfoxide (DMSO), 1a, formally as resonance contributor 1b, with oxalyl chloride, 2. The first intermediate, 3, quickly decomposes giving off CO2 and CO and producing dimethylchlorosulfonium chloride, 4.



After addition of the alcohol 5, the dimethylchlorosulfonium chloride 4 reacts with the alcohol to give the key alkoxysulfonium ion intermediate, 6. The addition of at least 2 equivalents of base ¡ª typically triethylamine ¡ª will deprotonate the alkoxysulfonium ion to give the sulfur ylide 7. In a five-membered ring transition state, the sulfur ylide 7 decomposes to give dimethyl sulfide and the desired ketone (or aldehyde) 8.

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5Â¥2012-08-28 14:02:12
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