A New Method for the Conversion of Optically Active Alcohols to Halides with Inversion of Configuration

Imidates

“…16) [27]. In water, the imidate salts hydrolyze to the corresponding esters and ammonium salts ( E q .…”

“…Methanol and ethanol are the most widely used alcohols in the Pinner synthesis, as seen in Table I; however, propyl [32], isopropyl [33], butyl [32], isobutyl [ l a ] , sec-butyl [27], octyl [34], decyl [34], and benzyl [35a] alcohols have also given satisfactory results. More-recent examples of the usefulness of the Pinner reaction are worth consulting [35b,c,d,e].…”

“…• CN-C-OC2H5 + C2H5O-C-C-OC2H5 (27) In 1896 Hesse [57] and in 1899 Hessler [58] reported a similarly easy base-catalyzed formation of imidates from substituted malonitriles. This reaction was further extended by Stieglitz [59a-d] and Acree [42a, 60] and their collaborators.…”

Die Reaktion von Carbonsäuren mit Acetalen des N, N‐Dimethylformamids: eine Veresterungsmethode

“…C,,H,,O,N Ber. C 72,40 H 8,71 N 2,810/,,72,31 ,,8,68 ,,2,78y0 ,,498 (in CH,Cl,) L-Valin-benzyZester-hydro~hZor~d. 590 mg (1,18 mMol) des obigen N-nOBC-L-valin-benzylcsters (Smp.…”

“…0,415 g (3,4 mMol) Benzoesaurc, 0,835 g (4,l mMol, 1,2 Aquiv.) (+)-DMF-di-sec-butylacetal ([a]: = + 36,4'),8 ml frisch destilliertcs Benzol, 2 Std./8Oo unter N, (allg. Verfahren zur Veresterung der Benzoesaure rnit DMF-Acetalen, vgl.…”