62533-55-5Relevant academic research and scientific papers
A general and stereoselective method for synthesis of tri- and tetrasubstituted alkenes
Macia?giewicz,Dybowski,Skowrońska
, p. 6057 - 6066 (2007/10/03)
A convenient, general and stereoselective synthesis of trisubstituted alkenes and tetrasubstituted alkenes containing a cyanide function as well as trisubstituted episulphides have been elaborated. Methodology described for the preparation of these compounds is based on the corresponding readily available selenophosphates 1 and thiophosphates 2.
Dipole-Stabilized Carbanions from Thioesters. Secondary α'-Lithio Carbamates and Tertiary α'-Lithio Thioesters
Beak, Peter,Becker, Peter D.
, p. 3855 - 3861 (2007/10/02)
The formation of 5 and 17, synthetic equivalents of the α-lithioalkylthio and α-lithiodialkylthio functions, respectively, by deprotonations of the corresponding carbamate 4 and thioester 16 are reported.The reactions of these formally dipole-stabilized carbanions with a variety of electrophiles and their use in synthese of 2,3-substituted thiiranes are demonstrated.The rearrangement of 17 to an α-thiol ketone is shown to be intramolecular by a double labeling experiment.Potentially chiral or conformationally isomeric α'-lithio thioesters are found to be racemized and equilibrated.Formations of secondary α'-lithio thioesters in medium chain, β'-dimethylamino, and allyl systems are reported while β'-alkoxy groups are shown to eliminate to give vinyl thio esters which undergo further metalation.The kinetic acidity of a methyl thioester is shown to be comparable to a propenyl thioester and greater then an ethyl thioester.
Metalated Nitrogen Derivatives of Carbonic Acid in Organic Synthesis, XVII. - Conversion of 2-Methylimino-1,3-oxathiolanes into Thiiranes
Hoppe, Dieter,Follmann, Rainer
, p. 1779 - 1785 (2007/10/02)
2-Methylimino-1,3-oxathiolanes 3, readily obtained from lithiated S,S'-dialkyl N-(methyl)imidodithiocarbonates 1 and carbonyl compounds 2, were transformed into thiiranes 6 via N,N-dimethyl-N-(1,3-oxathiolan-2-ylidene)ammonium iodides 7.With exclusion of 5-aryl-substituted compounds 3 the reaction proceeds highly diastereoselectively.
