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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: lethal_lefty on March 08, 2007, 01:02:18 AM

Title: synthesis of diethyl sulphone
Post by: lethal_lefty on March 08, 2007, 01:02:18 AM

hey guys, i'm having a bit of trouble on a particular problem for a review for my organic chemistry exam on friday.

i need to come up with a synthesis that will yield diethyl sulphone, and i can't for the life of me figure out how to do it.  i've been hittin the book for about 4 hours now, so it's possible that i'm just having a brain fart and making this way more difficult then it actually is.

i know that i came up with a synthesis which yields methyl ethyl sulphone, but unfortunately that isn't my desired product.  regardless, i'll post what i came up with for the methyl ethyl sulphone and if you guys could help me piece together what i need to do to get diethyl sulphone i'd greatly appreciate it.

Here goes:  CH₃CH₂SNa + CH₃I ---> CH₃CH₂SCH₃ + H₂O₂  --->  CH₃CH₂S=OCH₃  (i don't know how to properly write the double bond between the S and O, but the methyl group is attached to the S not the O, sorry if it's hard to decipher)   that will leave me with a sulphoxide, then by once again reacting my sulphoxide with H₂O₂ i'll have my methyl ethyl sulphone.

is there a simple way to tack another methyl group on the methyl side of the sulphone in order to yield a diethyl sulphone or am i going about this synthesis all wrong?

again, i hope you guys can decipher what my reactions were supposed to be, i tried to write it out as plainly as possible but i couldnt think of a way to clearly show the double bond without it appearing confusing.

Title: Re: synthesis of diethyl sulphone
Post by: Dan on March 08, 2007, 03:57:37 AM

Instead of MeI, you could use something else...

Title: Re: synthesis of diethyl sulphone
Post by: AWK on March 08, 2007, 04:42:40 AM

Think about oxidation of diethylthioether