Preparation of polyenes
AssigneeMassachusetts Institute of Technology
InventorsGeorge H. Buchi, Roger M. Freidinger
Life of this patent
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Abstract
Polyenes are synthesized from unsaturated materials having allylic hydroxyl groups, which react with imidosulfides to produce sulfones. Removal of the sulfone group, e.g. by reaction with alkyllithium and iodine, results in compounds in which the allylic carbons are joined by a double bond. The reactions take place easily over wide temperature ranges. The method is particularly advantageous in the synthesis of carotenoids from polyene alcohols, being much simpler and easier to use than previous carotenoid syntheses.
Claims17
A method of preparing polyenic organic compounds, comprising reacting an allyl alcohol with a sulfide of the following formula
- R' -- S -- R"
- in which R' and R" are the same or different nitrogen-containing substituents, bound to sulfur through a nitrogen atom, the remainder of R' and R" being electrophilic, to produce an allylic sulfone, reacting said sulfone with an organometallic compound selected from the group of alkyllithiums and alkali metal amides and a halogen selected from the group of bromine, chlorine and iodine.
A method of preparing carotenoids, comprising reacting an allyl alcohol having the following formula:
- ##EQU5## wherein R.sub.1 represents from about 1 to 6 isoprene units, with a sulfide having the following formula:
- R.sub.2 -- S -- R.sub.3
- in which R.sub.2 and R.sub.3 are the same or different nitrogen-containing substituents, bound to sulfur through a nitrogen atom, the remainder of R' and R", being electrophilic, to produce a mixture comprising an allyl sulfone and sulfinate ester, converting said sulfinate ester to an allyl sulfone, reacting said sulfone with an organometallic compound selected from the group of alkyllithiums and alkali metal amides and a halogen selected from the group of bromine, chlorine and iodine.
Dependencies are inferred from the claim text.