|Oppolzer's Camphorsultam and Arndt-Eistert
||[Oct. 27th, 2012|04:13 pm]
My supervisor has given me a reaction from before I started my PhD to talk through during a presentation and I'm considering questions that may be asked in the Q&A. I'm struggling to work out how Oppolzer's camphor sultam works. I found one explanation that said "steric hindrance of the dimethyl group in conjunction with repulsion of the amide nitrogen lone pair". I just wanted to make sure that's right, as I've only found descriptions of selectivity when a sulfone oxygen coordinates to a Lithium enolate, whereas I have a silyl enol ether in my actual reaction.
Also, does anyone know why sonication and a catalyst would be needed for an Arndt-Eistert reaction? I thought the reaction happened pretty easily?
Thanks so much in advance :)