Phenyl-2-propyn-l-ol

F. B. Growcock and V. R. Lopp. The inhibition of steel corrosion in hydrochloric acid with 3-phenyl-2-propyn-l-ol. Corrosion Sci, 28(4) 397-410,1988. 

The catalytic propargylic alkylation was investigated in the presence of thiolate-bridged diruthenium complexes as catalysts generated in situ from reactions of [Cp RuCl(p2-Cl)]2 with optically active thiols prepared from the corresponding optically active alcohols [27]. Typical results for the reaction of 1-phenyl-2-propyn-l-ol with acetone in the presence of a variety of catalysts are shovm in Scheme 7.19. 

Minn, K (1991) Chalcones via a palladium-catalyzed coupling of iodoheterocycles to l-phenyl-2-propyn-l-ol. Synlett 115-116... 

Enantioselective Addition of Alkynyllithium to Aldehydes. The enantioselective addition of alkynyllithium to aldehydes in the presence of (1) provides optically active propargylic alcohols. (5)-l-Phenyl-2-propyn-l-ol with 92% ee is obtained in 87% yield from the enantioselective addition of Lithium (Trimethylsi-lyl)acetylide to PhCHO in the presence of (1) and the subsequent removal of the MesSi group (eq 3). "... 

Phenyl-2-propyn-l-ol was purchased from Lancaster Synthesis Ltd. and used as received. 1-Propanethiol was purchased from Aldrich Chemical Company, Inc., and used as received. 

The optical yield of the resulting l-phenyl-2-propyn-l-ol was determined by KX) MHz H-NMR ... 

Ethylenic and acetylenic alcohols can be converted into ketones or aldehydes by a mild reaction at room temperature, which consists of shaking them in an inert solvent such as petrol, chloroform, benzene, or acetone with a synthetic Mn02 H20.446 The reaction is highly recommended for oxidation of hydroxyl groups in sensitive compounds l-phenyl-2-propyn-l-one is thus obtained in 67.6% yield from l-phenyl-2-propyn-l-ol.447... 

Finally, the same complex was obtained by reacting hex-l-en-3-yne with Fe3(CO)i2 experimental TLC evidence showed that it was formed by splitting of water into its three components. This reaction should be compared with the dehydration of l-phenyl-2-propyn-l-ol HC2C(FI)Ph(OH) on Fe3(CO)i2 (Section... 

Figure 23. Comparison of the reactions of hex-3-yne and l-phenyl-2-propyn-l-ol with Fe3(CO)i2. Formation of ferrole derivatives upon splitting of water or of methanol.

Formal insertion of CO2 into Fe-C bonds is formed in the reaction of Fe3(CO)i2 with hex-l-en-3-yne. The reaction consists in the splitting of water into its three components, favored by the tic silica used for purification. The final product is, however, a binuclear complex.Related to this behavior is the reaction of Fe3(CO)i2 with l-phenyl-2-propyn-l-ol where the allenylidene complex Fe3(GO)9(/x-GO) C=C=C(H)Ph 4 is obtained first. It reacts with methanol to form a ferrole-like methoxycarbonyl (or acetate) derivative. It has been also observed that similar binuclear complexes can be obtained by reacting Fe3(CO)i2 with propargyl alcohol or propargyl chloride in KOH/CH3OH solutions followed by acidification with HCl GO and methanol activation occurs in this instance to form binuclear methoxycarbonyl derivatives and the open cluster Fe3(GO)io H2GGG(H)G(=0)G[GH2(0)GH3GGH2] 5. ... 

Like Grignard reagents, " organolithiums can add onto the triple bond of propargylic alcohols. Thus, -butyllithium combines with 3-phenyl-2-propyn-l-ol to give, after hydrolysis, 2-butyl-3-phenyl-2-propen-l-ol almost quantitatively. ... 

Water soluble mthenium(II) complexes [RuCl2(t -arene)(L)] [L = PTA (61), (PTA-Bz)Cl (62), DAPTA (63), TPPMS (64) t/ -arene = CgMee (a), 1,3,5-CeHaMea (b), p-cymene (c), CgHg (d)] were used by Cadiemo et al. [60] as catalysts for the synthesis of [i-oxo esters, important precursors for industrially relevant a-hydroxy ketones, by addition of terminal propargylic alcohols to carboxylic acids in aqueous medium. As a model reaction, l-phenyl-2-propyn-l-ol (1 mmol) was reacted with benzoic acid (1 mmol) in 1 mL of water in the presence of 2 mol % of Ru complex and stirred at 60 °C for 24 h. The best results were obtained with the TPPMS complexes (76-87% yields) whereas lower yields (14-71%, the latter in the presence of 61a) were observed for the PTA-type catalysts. 

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