The Preparation and Deamination of Some 1,3-Amino Alcohols

Abstract

Preparation and Deamination of 1,3-Amino Alcohols 4057 Analytical Method.-The product from each cleavage reaction was carefully rectified to remove the lower boiling alcohol. The end-run fractions were analyzed quantitatively by their infrared spectra by a slight modification of the technique described previously.1 In the case of a mixture of 3-ethoxy-l, 1, l-trifluoro-2-butanol (VII) and 3ethoxy-4,4,4-trifluoro-2-butanol (IX), a base line was drawn across absorption minima characteristic of both spectra at 6.05 and 13.35 µ. A calibration curve was established on the basis of the ratio of the distance measured from the base line to the absorption minimum at 10.3 µ and to the curve at 11.5 µ. The latter point is an absorption minimum for VII and an absorption maximum for IX. The calibration data are summarized in Table II.

Phenyl selenide anion, a superior reagent for the SN2 cleavage of esters and lactones

“…Physical and Spectral Data. For 4: mp 56-58 °C; NMR (CDClg) 10.50-9.90 (br s, 1), 7.70-7.12 (m, 5), 3.10-270 (t, J = 6 Hz, 2), 2.52-2.13 (t, J = 6 Hz, 2), 2.01-1.60 (m, 4); IR (CHClg) 1700 cm"1; mass spectrum, m/e 256, 258; precise mass caled for CnH140278Se m/e 256.01665, found 256.02362. For 6: yellow oil; NMR (CDClg) 10.37-10.10 (br s, 1), 7.70-7.12 (m, 5), 3.12-2.83 (t, J = 7 Hz, 2), 2.64-2.40 (t, J = 6 Hz, 2), 2.27-1.84 (m, 2); IR (CHClg) 1705 cm"1; mass spectrum, m/e 242,244; precise mass caled for CioH^Og^Se m/e 244.00020, found 244.00038.…”

“…Hz, 1),1.65-1.40 (d, J = 7Hz,3).For 35: yellow oil; NMR (CDClg) 7.63-7.00 (m, 5), 3.04-2.80 (t, J = 7 Hz, 2), 2.70-2.40 (t, J = 6 Hz, 2), 2.20-1.77 (m with overlapping s, 5); IR (CHClg) 1708 cm"1; mass spectrum, m/e 240, 242; precise mass caled for CnHuO^Se m/e 242.02096, found 242.01948.For 37: yellow oil;…”

C‐C‐Fragmentierung: Herkunft und jüngste Anwendungen

“…In den frühen 1950er Jahren erweiterten English und Mitarbeiter die Anwendungsbreite säurekatalysierter Spaltungsreaktionen von 1,3‐Diolen und erkannten die Bedeutung des kationischen Intermediats 65 (Schema ) 66. English und Bliss bemerkten 1956, dass andere Verbindungen, die β‐Hydroxycarbokationen erzeugen können, ebenfalls Fragmentierungen eingehen sollten 69. Entsprechend untersuchten sie die Desaminierung von 1,3‐Aminoalkoholen durch salpetrige Säure (z.…”

The Diastereomers of 1,3-Diphenyl-1,2-propanediol

“…130°,13 128-130°,14 and 129°. 16 Interestingly, dl-V undergoes spontaneous resolution on recrystallization from methanol,13 affording samples having m.p. >130°.…”