Wu, T. C. published the artcileAddition of silylmetallic compounds to olefins, COA of Formula: C12H10F2Si, the publication is Journal of Organic Chemistry (1960), 596-8, database is CAplus.
Ph3SiK (I) and Ph3SiLi (II) added to the olefinic linkage of 1,1-diphenylethylene (III) and of triphenylethylene (IV). No addition occurred, under corresponding conditions, to tetraphenylethylene (V) and to a variety of aliphatic and alicyclic olefins. For comparison purposes, triphenyl(1,1-diphenylethyl)silane (VI) and triphenyl(1,1,2-triphenylethyl)silane (VII) were synthesized by metalation of triphenyl(diphenylmethyl)silane (VIII) with BuLi and subsequent treatment with Me2SO4 and PhCH2Cl (IX), resp. I suspension (from cleavage of 0.01 mole hexaphenyldisilane) left 2 hrs. with 3.6 g. III in 20 ml. Et2O, the mixture hydrolyzed, the solution dried, and Et2O evaporated gave 3.5 g. triphenyl(2,2-diphenylethyl)silane (X), lustrous plates, m. 106-8¡ã (alc.). II (0.0122 mole) in tetrahydrofuran (THF) added to 2.2 g. III, the mixture stirred 0.5 hr. at room temperature, then hydrolyzed, the organic layer evaporated, and the residue recrystallized gave 80% X. Ph2CHCH2Cl (4.3 g.) in 20 ml. Et2O added during 2 min. to an amalgamated suspension of 0.02 mole I, the mixture left 2 hrs., hydrolyzed, and the product isolated gave 1.1 g. hexaphenyldisilane. The Et2O solution on evaporation gave 4.1 g. X. PhLi (0.002 mole) in THF added to 0.5 g. triphenyl-¦Â-styrylsilane, stirred 2 hrs. at room temperature, the mixture hydrolyzed, Et2O added, the solvent removed, and the residue chromatographed on Al2O3 gave 0.18 g. Ph4Si. No other product was isolated from the mother liquor. BuLi (0.015 mole) added at once to 5 g. VIII in 25 ml. THF, the solution stirred 40 min. at room temperature, excess Me2SO4 added, then hydrolyzed, and the product separated gave 58% VI, m. 193-5¡ã (C6H6-alc.). II (0.020 mole) in THF added to 5.12 g. IV, the mixture stirred 1 hr. at room temperature, hydrolyzed, and the organic layer worked up as usual gave 6.4 g. 1,2,2-isomer of VII, m. 171-2¡ã (C6H6-alc.). BuLi (0.015 mole) added to 5 g. VIII in 25 ml. THF, stirred 40 min. at room temperature, excess IX added, the mixture hydrolyzed, and worked up gave 1.5 g. VII, m. 198-200¡ã (C6H6-alc.). II (0.015 mole) in THF stirred 6 hrs. at room temperature with 5 g. V, then 1 hr. at 50¡ã, hydrolyzed with dilute acid, and the organic portion worked up gave 4.2 g. V, m. 222-4¡ã; the filtrate chromatographed gave 2.2 g. Ph3SiH, m. 43-5¡ã (MeOH). Attempted reactions of I with other olefins were carried out by mixing a suspension of I with an equimolar amount of the olefinic compound; the mixture stirred a certain time, H2O added, the organic layer dried, evaporated, and the residue crystallized gave triphenylsilanol (XI) as chief product. In 2 experiments with 1,2-dimethoxyethane as the solvent, a mixture of V and hexaphenyldisiloxane was also obtained. In the reaction of 9,9′-bifluorene with I in Et2O, heat was evolved and the mixture became dark. The workup gave a tarlike material from which little pure product could be isolated. The following results were obtained with I (olefin, reaction time in hrs., % yield of XI, and other products isolated given): 1-octene, 96, 63, -; 1-octene, 48, 25, 24% Ph4Si, 22% (R3Si)2O (XII); 1-dodecene, 72, 78, -; 1-dodecene, 48, 21, 36% R4Si, 20% XII; 1-hexadecene, 24, 86, -; 1-octadecene, 24, 89, -; cyclohexene, 48, 87, -; cyclohexene, 48, 66, -; 1-methylcyclopentene, 48, 72, -; 1,1-diphenylethylene, 2, -, 42% adduct; V, 48, 74, 70% R2C:CR2; V, 3, 52, 74% R2C:CR2; 1,4-diphenyl-1,3-butadiene, 5, 42, 12% (R3Si)2; 9,9′-bifluorene, 3, -, tar.
Journal of Organic Chemistry published new progress about 312-40-3. 312-40-3 belongs to catalysis-chemistry, auxiliary class Organic Silicones, name is Difluorodiphenylsilane, and the molecular formula is C3H5F3O, COA of Formula: C12H10F2Si.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia