Claesson, Alf published the artcileAllenes and acetylenes. X. Convenient method for conversion of acetylenic derivatives into conjugated dienes via α-allenic alcohols, Safety of 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, the publication is Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry (1975), 29(5), 609-16, database is CAplus.
4-Alkoxy- and 4-(tetrahydro-2-pyranyloxy)-2-butyn-1-ols are in most cases quantitatively converted into conjugated dienes when treated with LiAlH4 in refluxing THF or similar solvents. The reactions proceed via α- allenic alcohols. The dienes are free from positional isomers and the formation of alkenynes, which occurs in some cases, can be completely suppressed by a combination of LiAlH4 and AlCl3. Most of the conjugated dienes seem to be formed with low stereoselectivity. The E,E form is the predominant isomer of 2,4-hexadiene while of 4,6-decadiene the E,Z isomer predominates. These latter results may indicate that the attack by hydride on the central carbon atom of the propadienyl group is sterically hindered when the double bond remaining in the same position is formed with E configuration.
Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry published new progress about 27943-46-0. 27943-46-0 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Alkynyl,Ether, name is 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, and the molecular formula is C10H16O2, Safety of 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran.
Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics