Studies in stereochemistry. XL. Unusual magnitudes of optical rotations of imines of neopentylamine-1-d and ethylamine-1-d

New Lipophilic 2‐Amino‐N,N′‐dialkyl‐4,5‐dimethylimidazolium Cations: Synthesis, Structure, Properties, and Outstanding Thermal Stability in Alkaline Media

“…tert-Butyl azide, [16] neopentylamine, [27] and N,N'-dineopentyl-and N,N'-dicyclohexylthioureas [28] were obtained according to the literature procedures.…”

Practical One-Step Synthesis of Koga's Chiral Bases

“…Our results with a range of amine nucleophiles are presented in the Table. The preparation of each of Koga's chiral diamines (R)-2-4 proceeded in high yield (79-85%) and with stereochemical integrity 9 (entries 1-3). For the synthesis of diamine (R)-3, neopentylamine was prepared from pivalonitrile using a published procedure 10 and for the preparation of (R)-4, trifluoroethylamine was generated in situ from the corresponding hydrochloride salt using an extra equivalent of triethylamine. The 85% yield obtained for diamine (R)-3 (entry 2), arguably the most useful of the Koga bases, is particularly noteworthy.…”

Displacement reaction of neopentyl-1-d tosylate without rearrangement and optical rotatory dispersion spectra of chiral compounds with four different groups of either C3.nu. or C.inf..nu. symmetry attached to a central carbon

“…(R)-(-)-Neopentyl-/-i/ Bromide (4). ( 5)-Neopentyl-/-<f tosylate (9.75 g, 40 mmol) and anhydrous lithium bromide (3.47 g, 40 mmol) in HMPA (50 ml) were vigorously stirred at 110-115°under vacuum (25 mm) for 17 hr and the volatile products were collected as formed in a trap cooled by liquid nitrogen. The product was transferred under high vacuum to a second trap which could be stoppered and centrifuged.…”