Reaction of 1,3-Disubstituted Acetone Derivatives with Pseudohalides: A Simple Approach to Spiro[4.4]nonane-Type Bis-Oxazolidines and -Imidazolidines (Bicyclic Carbamates, Thiocarbamates, Ureas, and Thioureas)

Autor:	Jürgen Kopf, Robert Saul, Thorsten Kern, István Pintér, Peter Köll
Rok vydání:	2000
Předmět:	Oxazolidine chemistry.chemical_compound chemistry Bicyclic molecule Organic Chemistry Thio Organic chemistry Cyanamide Physical and Theoretical Chemistry Nonane Thiocarbamates Cyanate Imidazolidines
Zdroj:	European Journal of Organic Chemistry. 2000:205-209
ISSN:	1099-0690 1434-193X
DOI:	10.1002/(sici)1099-0690(200001)2000:1<205::aid-ejoc205>3.0.co;2-j
Popis:	Prochiral 1,3-dihydroxyacetone forms racemic oxazolidine- and oxazoline-type spiro[4.4]nonanes upon reactions with potassium (thio)cyanate and cyanamide. In contrast, 1,3-diaminoacetone yields only the corresponding spiro-bisimidazolidinethione under similar conditions together with monocyclic by-products, but the spiro-bisimidazolidinone is accessible by reaction of 1,3-dichloroacetone with urea. The resolution of the racemic spiro-bisoxazolidinethione 2a was achieved by using brucine as the resolving agent.
Databáze:	OpenAIRE
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