Re: Mitsunobu reaction: possible side reaction with sulfide?
Updated: 2011-08-31 16:53:30
Chemistry Cat flinches at the assortment of nucleophiles in your starting material.Chemistry Cat suggests you perform nucleophilic substitution of the phenol with mild base on your 2-tosylethanol, and then activate the alcohol later. Fewer things can go wrong.

Welcome to Cheap Laugh Tuesdays! (CLT) I always throw a cartoon or comic strip up on the screen before I start class to lighten the mood and give the students something to look forward to. After one year of teaching, I've developed quite a little collection of super awesome science & chemistry related cartoons. I'll [...]
Its reactors have been out of service for years, but Chernobyl Nuclear Power Plant’s vast electrical switchyard still buzzes with some of the highest voltages on the European continent. It’s a distribution hub that channels hundreds of megawatts generated at other plants to consumers in northern Ukraine and southern Belarus. The bustling control room for [...]
More interior photographs from the Chernobyl Nuclear Power Plant, this selection focusing on highlights of the Unit 1 control room and the building’s perhaps most distinguishing interior feature, its 600-meter-long “Gold Corridor.” Click any photo for a larger version with my description; click again for a full-size file. For this summer’s photos of the Unit [...]
I just returned from another trip to Chernobyl. We visited some parts of the power plant that we didn’t get to see on last year’s trip, but—as I’m sure my readers can understand—one day at the station wasn’t enough and I’m left pining for more! (I’m particularly lusting after a certain pachyderm appendage, if you [...]
Well... this oughta cover it. I was reading comments to my reddit submission of the many oxidation states of carbon, and Aa1979 asked if the functional groups could be arranged logically according to actual chemical transformations. I replied that would be too reaction dependent... alcohols can be turned into a great many things (chlorides, alkenes, [...]