dc.contributor.author | Sosa, Juan R. | en |
dc.contributor.author | Tudjarian, Armen A. | en |
dc.contributor.author | Minehan, Thomas G. | en |
dc.date.accessioned | 2018-07-12T22:28:19Z | |
dc.date.available | 2018-07-12T22:28:19Z | |
dc.date.issued | 2008 | en |
dc.identifier.citation | Organic Letters 10(21), 5091-5094. (2008) | en |
dc.identifier.issn | 1523-7052 | en |
dc.identifier.uri | http://hdl.handle.net/10211.3/204625 | en |
dc.description.abstract | α-Alkoxy ketones 3 can be transformed into 1-alkynyl ethers 5 by a two-step procedure involving formation of the enol triflate or phosphate and base-induced elimination. Performing the same reaction sequence with allylic alcohols (R2OH, R2 = allyl) furnishes instead γ,δ-unsaturated carboxylic acid derivatives 6, derived from [3,3]-sigmatropic rearrangement of the intermediate allyl alkynyl ethers at −78 °C and trapping of the subsequently formed ketene with nucleophiles (Nu-H). Benzyl alkynyl ether 5 (R2 = benzyl) rearranges to indanone 7 upon heating to 60 °C. | en |
dc.format.extent | 4 pages | en |
dc.language.iso | en | en |
dc.publisher | American Chemical Society | en |
dc.relation.uri | doi.org/10.1021/ol802147h | en |
dc.rights | copyright 2008 American Chemical Society | en |
dc.subject | Alkynes | en |
dc.subject | Amides | en |
dc.subject | Benzene | en |
dc.subject | Carboxylic Acids | en |
dc.subject | Esters | en |
dc.subject | Ethers | en |
dc.subject | Ketones | en |
dc.subject | Methylation | en |
dc.subject | Molecular Structure | en |
dc.subject | Temperature | en |
dc.subject | Alkynes | en |
dc.subject | Amides | en |
dc.subject | Carboxylic Acids | en |
dc.subject | Esters | en |
dc.subject | Ethers | en |
dc.subject | Ketones | en |
dc.subject | Benzene | en |
dc.title | Synthesis Of Alkynyl Ethers And Low-Temperature Sigmatropic Rearrangement Of Allyl And Benzyl Alkynyl Ethers | en |
dc.type | Article | en |
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