1595-53-5

Upstream product

• 590-37-4 2-methylpent-4-yn-2-ol 
• 28750-44-9 2-chloromethylene-1,1-dimethyl-cyclopropane 
• 115-11-7 isobutene 
• 74-86-2 acetylene 

Downstream Products

• 110211-74-0 phenylselenyl-5 TESoxy-3 (+/-) dihydrobisabolangelone (syn) 
• 110211-74-0 phenylselenyl-5 TESoxy-3 (+/-) dihydrobisabolangelone (anti) 
• 124456-72-0 acetoxy-3 methyl-5 (methyl-6 hydroxy-2 heptene-5 yne-3 yl)-2 TBDMSoxy-1 cyclohexane (1,3 trans) 
• 30557-81-4 (+/-) bisabolangelone 
• 1585-01-9 5-Methyl-1-phenylhex-4-en-2-in-1-on 
• 56155-47-6 3-Phenylamino-1-phenyl-5-methyl-2,4-hexadien-1-on 
• 81052-99-5 cleviolide 
• 110211-65-9 (1R,2R,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-1-hydroxy-1,5-dimethyl-hex-4-en-2-ynyl)-5-methyl-cyclohexanol 
• 110211-65-9 methyl-5 (hydroxy-2 methyl-6 heptene-5 yne-3 yl)-2 TBDMSoxy-1 cyclohexanol-3 
• 58275-93-7 2-Methyl-2-hexen-4-in 
• 1791-19-1 5-methyl-1-phenylhex-4-en-2-yn-1-ol 
• 854901-62-5 1-(4-methyl-pent-3-en-1-ynyl)-cyclohexanol 

Relevant academic research and scientific papers

Reaction rate and isomer-specific product branching ratios of C 2H + C4H8: 1-butene, cis -2-butene, trans -2-butene, and isobutene at 79 K

The reactions of C2H radicals with C4H8 isomers 1-butene, cis-2-butene, trans-2-butene, and isobutene are studied by laser photolysis-vacuum ultraviolet mass spectrometry in a Laval nozzle expansion at 79 K. Bimolecular-reaction rate constants are obtained by measuring the formation rate of the reaction product species as a function of the reactant density under pseudo-first-order conditions. The rate constants are (1.9 ± 0.5) × 10-10, (1.7 ± 0.5) × 10 -10, (2.1 ± 0.7) × 10-10, and (1.8 ± 0.9) × 10-10 cm3 s-1 for the reaction of C2H with 1-butene, cis-2-butene, trans-2-butene, and isobutene, respectively. Bimolecular rate constants for 1-butene and isobutene compare well to values measured previously at 103 K using C2H chemiluminescence. Photoionization spectra of the reaction products are measured and fitted to ionization spectra of the contributing isomers. In conjunction with absolute-ionization cross sections, these fits provide isomer-resolved product branching fractions. The reaction between C2H and 1-butene yields (65 ± 10)% C4H4 in the form of vinylacetylene and (35 ± 10)% C5H6 in the form of 4-penten-1-yne. The cis-2-butene and trans-2-butene reactions yield solely 3-penten-1-yne, and no discrimination is made between cis- and trans-3-penten-1-yne. Last, the isobutene reaction yields (26 ± 15)% 3-penten-1-yne, (35 ± 15)% 2-methyl-1-buten-3-yne, and (39 ± 15)% 4-methyl-3-penten-1-yne. The branching fractions reported for the C2H and butene reactions indicate that these reactions preferentially proceed via CH3 or C2H3 elimination rather than H-atom elimination. Within the experimental uncertainties, no evidence is found for the formation of cyclic species.

Synthesis of cleviolide and the scobinolides

The palladium-catalysed cross-coupling reaction of 4-tributylstannylfuran-2(5H)-one 3 with 1-iodo-4-methylpent-3-en-1-yne 4a gives the natural product cleviolide; from this substance may be prepared both (Z)- and (E)-isomers of scobinolide.