Phenylacetylide

Methyl propiolate and pyridine give a rather unstable 2 1 molar adduct which is the 1,2-dihydropyridine (112). The reaction sequence proposed to account for its formation is identical in principle to a similar scheme proposed earlier in the acridine series (Section II,A,2) and is also supported by the observation that the 1-benzoyl-pyridinium cation with the phenylacetylide anion yields (113). ... 

An unusual cyclization, which results in carbocycles rather than heterocycles, was described in (69JCS2453). The reaction between o-iodobenzamides and copper phenylacetylides in pyridine leads to indanone (74%) rather than tolane (Scheme 124). 

Clusters can be formed by reacting transition-metal complexes with group-IB derivatives. The reaction of Ir(COXPPh3)2CI with Cu phenylacetylide gives rise to two cluster products ... 

Sodium phenylacetylide 3-Buten-1-ynyidiethylaluminium Dimethyl-phenylethynylthallium 3-Buten-1 -ynyltriethyllead 3-Methyl-3-buten-1-ynyltrielhyllead 3-Buten-I-ynyldiisobutylaluminium Bis(Triethyltin) acetylene... 

Shieh, S.-J., Hong, X., Peng, S.-M. and Che, C.-M. (1994) Synthesis and crystal structure of a luminescent onedimensional phenylacetylide-gold(I) polymer with 2,6-bis(diphenylphosphino) pyridine as ligand. Journal of the Chemical Society, Dalton Transactions, 3067-3068. 

Attempts have been made to fix C02 using organometallic complexes in photochemical reactions. A reversible binding of C02 was achieved with the Cu(I) phenylacetylide-phosphine complex,208 which acted as a reversible C02 carrier at ambient temperatures and atmospheric pressure, by C02 insertion into the... 

Four equivalents of lithium phenylacetylide reacted with bis bis(trimethylsilyl)amido zinc (Scheme 51) to form the ion-paired dilithiotetra(phenylacetylido)zincate 65, whose structure is shown in Figure 33.121 The zinc-carbon bonds (2.05 A) are somewhat longer than those observed in the tri(phenylacetylido)zincate 62a, due to the increase in both the coordination number and the negative charge on the ion. Each lithium ion is associated with the zincate ion through coordination to two of the triple bonds. 

In 1972, Kinugasa and Hashimoto (841) reported the reaction of copper (I) phenylacetylide with a.A-diphenylnitrone in dry pyridine. It has provided an... 

Silver chloroacetylide, 0566 Silver cyclopropylacetylide, 1838 Silver 1,3,5-hexatrienide, 2052 Silver 3-hydroxypropynide, 1088 Sodium acetylide, 1022 Sodium bromoacetylide, 0581 Sodium chloroacetylide, 0601 Sodium ethoxyacetylide, 1478 Sodium methoxyacetylide, 1123 Sodium phenylacetylide, 2911 Strontium acetylide, 1026 Tetraethynylgermanium, 2895 Tetraethynyltin, 2901 Thallium iodacetylide, 0984... 

Phenyl(p-methoxyphenyltelluro)acetylene (typical procedure To a solution of lithium phenylacetylide (20.0 mmol), prepared as described above, is added dropwise a solution of p-methoxyphenyltellurenyl bromide (prepared by adding bromine (1.60 g, 10.0 mmol)) in benzene (5 mL) to a solution of the corresponding ditelluride (4.69 g, 10 mmol) in THF (10 mL) at 0°C under Nj. The reaction mixture is stirred for 1 h at room temperature and then treated as described above to give the product (4.90 g (73%)), which is recrystallized from EtOH (m.p. 71-72°C). 

Lithium phenylacetylide was trifluoromethylated with the less powerful Se-triflate 26 in high yield (Eq. 20). 

Wen and Grutzner used, among other NMR parameters, the QSC of the lithium enolate of acetaldehyde to deduce that it exists as tetramers of different solvation in THF and THF/n-hexane solvent systems . However, the most thorough study of Li QSC and the most interesting in the present context was reported by Jackman and coworkers in 1987167 -pjjg effects on the QSC values of both aggregation and solvation in a number of organolithium systems was studied in this paper, i.e. different arylamides, phenolates, enolates, substituted phenyllithium complexes and lithium phenylacetylide. 

With 2-unsubstituted quinazolines 426 (X = O or S), organometallic addition occurs at the 2-position to give 2-alkyl-l,2-dihydroquinazolines 428 <2005JSF121, 2005S2951>, while with 2-alkoxyquinazolines addition of orga-nometallics occurs at the 4-position, as demonstrated by the addition of lithium phenylacetylide to the 2-methoxy-methyl quinazolinone 429 which gave a quantitative yield of a tautomeric mixture of the 3,4- and 1,4-dihydro derivatives 430 and 431 <2004JA5427>. 

Preparation of l-Chloro-2-phenylacetylene from Lithium Phenylacetylide and Chlorine... 

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