Re: ORGLIST: (no subject)

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From: Jay (hi_buddy03$##$yahoo.com)
Date: Tue Jul 22 2008 - 12:21:14 EDT


Allan, You might want to look into these papers. P.A Greico JACS 99 7393 (1977) H. Hagiwara and H. Uda J. Chem Soc Chem Commun 1351 (1987) J. H. Babler JOC 43 1821 (1978) J. J Brown JACS 86 2183 (1964) Y. Kamitori Tetrahedron Letters 26 4767 (1985) Jay ----- Original Message ---- From: Macabeo Allan Patrick <allanpatrick_m$##$yahoo.com> To: Jay <hi_buddy03$##$yahoo.com> Sent: Saturday, July 19, 2008 7:06:31 AM Subject: Re: ORGLIST: (no subject)   Hi,   Thank you for the suggestions. Can you specify the equivlents of the reagents per mole of my substrate? My dioxolane is alehyde based. I referred to Kocienski but found methods 1 and 3, 4 not applied. Can you give me the lits? Tnx   Allan Suggestions for you Allan: 1) PPTS, Acetone, Water, reflux 2) 5% THF-HCl would require longer hours ~20-24h 3) 80% AcOH 65C 5-10min 4) Wet MgSO4 (C6H6, 20C, 1h) effects selectively, quantitative cleavage of an a,b-unsat 1,3-dioxolane in the pr of a 1,3-dioxolane.   FYI: Relative rates of hydrolysis of some dioxolanes [dioxolane:aq HCl (1:1) are as follows: 2,2-dimethyl dioxolane:2-methyldioxolane:dioxolane, 50,000:5,000:1.   Jay ----- Original Message ---- From: Macabeo Allan Patrick <allanpatrick_m$##$yahoo.com> To: everybody$##$orglist.net Sent: Sunday, July 13, 2008 1:52:29 PM Subject: ORGLIST: (no subject) I would like to ask if any of you have idea on the best conditions to deprotect dioxolane protected aldehydes. I have tried to cleave it using FeCl3.6H2O, THF-HCl and even oxidizing it to aldehydes but they are not working. Any suggestion?   Thanks,   Allan


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