73465-26-6Relevant academic research and scientific papers
Alkoxide-Promoted Rearrangements of 1,3-Dithianes
Wilson, Stephen R.,Misra, Raj N.,Georgiadis, Gregory M.
, p. 2460 - 2468 (2007/10/02)
The allylic alcohols formed from 1,2-addition of 2-lithio-1,3-dithianes to α,β-unsaturated ketones have been shown to undergo rearrangement to afford their respective Michael-addition products upon treatment with KH in HMPA/THF in some cases.The major side reaction and in some instances the sole reaction pathway was fragmentation.The rearrangement was applied to a two-carbon macrocyclic ring-expansion strategy which is illustrated in a synthesis of DL-muscone, a 15-membered-ring ketone, from cyclotridecanone.Attempts to induce a similar rearrangement by replacing the 1,3-dithiane group with a thiophenyl or 1,3-dithiolane group proved unsuccessful.
