[Balance87]

Okay - Im going to be honest and admit i have little education in chemistry. I skipped all but two of my sophomore chem labs. Still, ive developed an intense interest in medicinal plants. The chemistry stuff is secondary. I teach myself things, and im hoping that some people here will be patient enough to help me out. This stuff seems beyond your average high school chem lab, so i put it here. If its misplaced, i apologize.

Heres my mission - i'm working with an indole compound similar to yohimbine. I will be using PIFA to add a hydroxyl group to the 7 position (I hope im using correct terminology, im still shaky on the positions.) This should result in a 40-50% yield (i know it would be a higher &age in yohimbine, but its not as high for this) plus a small %age of a dimeric compound that will be discarded.

So, my series of questions: I would like to find a NEWER book about indole chemistry that might cover these types of things (hypervalent iodine specifically), so i can ask fewer questions later. Any suggestions? The literature i had been following used lead tetraacetate, and I'm uncomfortable with using that for a myriad of reasons.

The literature im following now pretty much shows two options for the PIFA reaction: one is in aqueous acetonitrile (which results in higher yields and a smaller %age of the dimeric compound,) and the other is in methylene chloride...that said, the literature is in japanese. Im hoping somebody can confirm this for me - is it worth trying with DCM? Id prefer to use that, because i could also use the DCM during chromatography. If im getting so many liters, i might as well use it for the reaction too.

Lastly - yeah, Im seriously inexperienced. I have done an easier type of oxidation before, but after reading about lead tetraacetate, im hesitant about using PIFA until i have better knowledge of how to use it and how safe it is. No matter what, its all getting run through the column in the end, so im hoping that somebody can give me a little real world experience and insight into what i should expect with this type of reaction. I know its safer than the alternative, but still.

These are my primary concerns. Be honest - tell me if you think i should get assistance. Any and all help is appreciated...

Seanus