Static and dynamic stereochemistry of tetra(primary alkyl)ethylenes

Abstract

Preparation of an Authentic Sample of 34. Hydroboration-oxidation of 478 mg (3.23 mmol) of the tricyclic olefin 35s and subsequent Collins oxidation of the resulting alcohols as described above gave two crude ketones 36 and 37 in an about 1:1 ratio (IR 1735 cm"1). Upon chromatography on activated alumina, only ketone 36 was isolated: 380 mg (72% from 35); mp 32 °C; IR (KBr) 1735 cm'1; MS, m/e (relative intensity) 164 (M+,

Experimental Investigation of the Primary and Secondary Deuterium Kinetic Isotope Effects for Epoxidation of Alkenes and Ethylene with m-Chloroperoxybenzoic Acid

“…The usual trend 2,26 in alkene reactivity was observed, namely that successive substitution of the double bond with alkyl groups enhances the rate of epoxidation. Where direct comparisons can be made, the results obtained here are in good agreement with kinetic data reported for epoxidation of aliphatic olefins with peracetic acid in acetic acid 26 and MCPBA in halogenated solvents. ,, …”

A Practical Method for Epoxidation of Terminal Olefins with 30% Hydrogen Peroxide under Halide-Free Conditions

“…1,2-Epoxyoctane. GC (column, OV-1, 0.25 mm x 50 m, GL Sciences Inc.); carrier gas, helium (1.2 kg/cm 2 ); initial column temp, 70 °C; final column temp, 280 °C; progress rate, 5 °C/min; injection temp, 280 °C; split ratio, 100:1; t R of 1-octene, 6.4 min; t R of 1,2-epoxyoctane, 10.7 min. 1 H NMR (400 MHz, CDCl 3 ) δ 0.89 (t, 3H, J = 6.8 Hz), 1.29−1.55 (m, 10H), 2.46 (dd, 1H, J = 2.9, 4.9 Hz), 2.74 (dd, 1H, J = 3.9, 4.9 Hz), 2.89 (br, 1H).…”

Protocol for determining enantioselective binding of chiral analytes on chiral chromatographic surfaces

“…MM2 accounts for this type of interaction because of its propensity to overestimate rr-face attractions between aromatic chromophores. 24 Finally the amide bonds were assumed to be planar and in the Z configuration.25…”