The Preparation of Substituted Styrenes by Methods Not Involving Hydrocarbon Cracking.

Vinylation of Aromatic Halides Using Inexpensive Organosilicon Reagents. Illustration of Design of Experiment Protocols

“…The reaction proceeded in all solvents tested, although DMF was slightly superior (average yields: toluene -11%, THF -12%, DMF -20%, dioxane -15%). The highest yield resulted from the combination of cesium hydroxide and DMVSOEt (9) in THF, with Pd (dba) 2 /AsPh 3 as the catalyst/ligand system, which afforded a 42% yield of 14a (GC analysis with internal standard). To verify the results, run #6 was repeated in a standard reaction apparatus using a small increase in vinyl donor (2.0 equiv) and activator (3.0 equiv).…”

“…7 Moreover, styrenes find increasing application for the development of olefin metathesis, both as substrates and as ligands for metal catalysts. 8 Although styrenes are classically prepared using the strongly basic conditions of dehydrohalogenation or dehydration, 9 the advent of metal-catalyzed, cross-coupling reactions has provided a range of milder methods for their preparation. This strategy involves the combination of an organometallic donor (generally a vinylmetallic species) with an organic acceptor (generally an aryl halide or pseudohalide) (Scheme 1).…”

The Olefin-Aldehyde Condensation. The Prins Reaction.

“…70 p.s.i.g. 100 per cent 0.96 83 per cent (on CH3CHO) 6 per cent (on CH3CHO) 34 per cent (on reacted isobutylene)…”

Oxidation by cobalt(III) acetate. Part 10. Effects of ring substituents on the product distributions in the oxidation of β-methylstyrenes by cobalt(III) acetate in acetic acid

“…Ring-substituted olefins were prepared by the dehydrations of the corresponding 1 -arylpropanols obtained by reduction of propiophenones over potassium hydrogensulphate under reduced pressure. 24 1 -(p-Methylpheny1)prop-1 -ene (1 b) had b.p. 97-98 "C at 30 mmHg; G(Cc14) 1.8 (d, 3 H), 2.3 (s, 3 H), 5.6-6.7 (m, 2 H), and 7.2 (s, 4 H).…”