Fig. 2. Scale-up and mechanistic study of EDD reaction.

a) Batch (4 gram) and flow (100 gram) scale-up of a key intermediate in the synthesis of (R)-muscone. b) Proposed mechanism of the EDD reaction based on observations. It is postulated that EDD proceeds through three elementary steps: (1) formation of the radical cation intermediate through direct anodic oxidation; 2) deprotonation of the radical anion intermediate to afford the allylic radical; 3) a second oxidation to form an oxonium intermediate. c) Experimental evidence for step 1. d) Experimental evidence for step 2. e) Experimental evidence for step 3. f) Prediction of reactivity based on ¹H NMR chemical shift. ^aYield based on LCMS conversion.