Tert-Butylphenylacetylene

Newman, M.S. and Lee, L.F. 1972. The synthesis of arylacetylenes. 3, 5-Di-tert-butylphenylacetylene, J. Org. Chem., 37 4468 1469. This aldehyde was used in order to increase the solubility of the final product. 

These alkynes do not undergo such smooth dimerizations to alkadiene derivatives such as 21 or 22 when sodium or potassium is employed or when the reaction is conducted in other solvents (27-30). The potassium adduct of tert-butylphenylacetylene (cf. 13) dimerizes through the para-position of the phenyl group (35). These observations indicate that the special reactivity of lithium may reside in the greater autoassociation tendency of its radical-anion adducts (20a). 

Zhang H, Lin HL, Walker VJ, Hamdane D, Hollenberg PF (2009) tert-Butylphenylacetylene is a potent mechanism-based inactivator of cytochrome P450 2B4 inhibition of cytochrome P450 catalysis by ste-ric hindrance. Mol Pharmacol 76 1011-1018... 

Lin H-L, Zhang H, Jushchyshyn M, Hollenberg PF (2010) Covalent modification of Thr 302 in CYP2B1 by the mechanism-based inactivator 4-tert-butylphenylacetylene. J Pharmacol Exp Ther... 

REDUCTIVE DIMERIZATION OF TjERT-BUTYLPHENYLACETYLENE. Under nitrogen, a freshly cut suspension of lithium pieces (138 mg, 20 milligram-atoms (mg-at) of wire cut in 2.0-mm segments) in 3.16 g (20 mmol) of tert-butylphenyl-acetylene and 20 mL of ethyl ether was stirred vigorously as 1.2 mL of THF was added dropwise at 25 °C. During the following 3 h, the solution became red, and the amount of lithium diminished. The lithium was removed, and the red solution was treated with water (about 60 mg of Li was recovered). The mixture... 

---