ISSN:
0170-2041
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Metalated Nitrogen Derivatives of Carbonic Acid in Organic Synthesis, XVII. - Conversion of 2-Methylimino-1,3-oxathiolanes into Thiiranes2-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.
Notes:
Die 2-Methylimino-1,3-oxathiolane 3, erhalten aus den lithiierten N-(Methyl)imidodithiokohlensäure-S,S′-dialkylestern 1 und Carbonylverbindungen 2, wurden über N,N-Dimethyl-N-(1,3-oxathiolan-2-yliden)ammoniumiodide 7 in Thiirane 6 umgewandelt. Mit Ausnahme 5-arylsubstituierter Verbindungen 3 verläuft die Reaktion hochdiastereoselektiv unter Retention der Konfiguration.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.198019801117
