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Topic: Carey & Sundberg question  (Read 9999 times)

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Offline MissPhosgene

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Re: Carey & Sundberg question
« Reply #15 on: May 06, 2010, 01:04:22 AM »
yeah, that is true. However, what I want to know is why Hg(OAC)2 and LiClO4 were also put in the pot.
Stereograms of the 32 crystallographic point groups: little bike wheels of cold, hard, pure rationality.

Offline AWK

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Re: Carey & Sundberg question
« Reply #16 on: May 06, 2010, 06:11:31 AM »
Authors suggest
PHSCl * Hg(C2H3O2)2 = PhSOCOCH3 since starting from  pure (though unstable) PhSOCOCH3 they got a better yield 70 % with cyclohexene (instead of 50 %  in this method).
Reaction without CH3CN gave acetate instead of acetimidate.
see also
N. S. Zefirov, N. K. Sadovaja, A. M. Maggerramov, !. V. Bodrikov, and V. R. Kartashov,. Tetrahedron, 31, 2948 (1975)

Use of LiClO4 is disccussed in
Snezana Dalipi, George H. Schmid,. J. Org. Chem., 1982, 47 (25), pp 5027–5029

Edit: formatting corrected.
« Last Edit: May 06, 2010, 08:01:18 AM by Borek »
AWK

Offline MissPhosgene

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Re: Carey & Sundberg question
« Reply #17 on: May 06, 2010, 07:23:29 PM »
Thanks! That's awesome.  :)
Stereograms of the 32 crystallographic point groups: little bike wheels of cold, hard, pure rationality.

Offline pacifyer

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Re: Carey & Sundberg question
« Reply #18 on: May 12, 2010, 07:01:35 PM »
I think Hg+ as electrophile adds to the double bond as the first step...  ;)

Offline MissPhosgene

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Re: Carey & Sundberg question
« Reply #19 on: May 12, 2010, 09:13:30 PM »
Pacifyer I think that's a good possibility. There are a few ways to get a mechanism that looks reasonable.
Stereograms of the 32 crystallographic point groups: little bike wheels of cold, hard, pure rationality.

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