77549-98-5Relevant academic research and scientific papers
EPOXYANNULATION II: CYCLIZATION OF ω-kETOSULFONIUM SALTS
Garst, M. E.,Johnson, A. T.
, p. 4811 - 4814 (1980)
Treatment of 1,5 or 1,6 ketosulfonium salts with potassium t-butoxide has yielded cyclic epoxides of high stereochemical purity in good yield.
Epoxyannulation. 4. Reactions of 1,5-, 1,6-, and 1,7-Oxosulfonium Salts
Garst, Michael E.,McBride, Bill J.,Johnson, Alan T.
, p. 8 - 16 (2007/10/02)
Treatment of six 1,5- and 1,6-oxosulfonium salts with potassium tert-butoxide affords an oxabicyclohexane, an oxabicycloheptane, hydrindan oxides, or a decalin oxide in 55-95percent yield.The stereoselectivity of this reaction ranges from 75percent for the formation of (1α,3α,7α)-2-oxatricyclo1,3>decane (21) to greater 99percent for (1α,2α,7α)-2-oxatricyclo1,3>decane (14) and for (1α,2α,8β)-2-oxatricyclo1,3>undecane (25).Five 1,7-oxosulfonium salts, one 1,8-salt, and one 1,11-salt and base give only elimination products.The sulfonium salt from 2-cyclopentanone (29) provides 3-methylspirodec-2-en-6-one (30) in 40percent yield.The salt from 2-cyclohexanone (32) yields 38percent of 4-methylbicycloundeca-1(7),3,5-triene (33).
