Highly Branched Molecules. III. The Preparation of Tri-t-butylcarbinol by Means of t-Butyllithium

Solvolytic Displacement Reactions At Saturated Carbon Atoms

“…The rates of the acid-catalyzed solvolyses in 75 per cent aqueous methanol of the p-nitrobenxoates of tri-tert-butylcarbinol (CLXIV) and tert-butyl alcohol are in the ratio 50,000: 1 (47). Tri-tert-butylcarbinyl derivatives are very strained; the strain is readily apparent in Stuart models of the compounds by the ease with which the models tend to fall apart.…”

Synthesis of 13,14-dialkylpicenes and hindered rotation of the alkyl groups as studied by dynamic NMR spectroscopy and molecular mechanics calculations

“…I s These alcohols were obtained from 1-bromonaphthalene and the appropriate aldehyde using n-butyl-lithium in solution. [9][10][11][12][13][14][15][16][17][18][19][20][21]…”

Remote secondary deuterium kinetic isotope effects as a probe of steric strain in the solvolysis of tertiary alkyl carbinyl systems

“…After cooling, a Teflon coated stir bar was placed in the flask with 0.44 g of lithium sand containing 4% sodium. 57 The lithium sand was rinsed with two 15-mL portions of anhydrous diethyl ether and suspended in 15 mL of diethyl ether, tert-Butyl chloride (2.00 g, 0.02 mol) was placed in the addition funnel and a few drops were added neat to the lithium suspension at room temperature. After the solution was stirred for a few minutes a precipitate began to form and the flask was immediately cooled to -35 °C.…”