38154-03-9Relevant academic research and scientific papers
A Convenient Method for the Preparation of Bicyclic Dihydro-1,4-dioxins, Dihydro-1,4-oxathiins, Dihydro-1,4-dithiins and Related Compounds
Fjeldskaar, Inger Reidun,Rongved, Paul,Skatteboel, Lars
, p. 477 - 486 (2007/10/02)
Acid catalysed reactions of cyclic α-hydroxy ketones with ethylene glycol, 2-mercaptoethanol and 1,2-ethanedithiol furnished in most cases the corresponding dihydro-1,4-dioxin, dihydro-1,4-oxathiin and dihydro-1,4-dithiin derivatives, respectively, in high yields.Similar reactions of 2-hydroxycyclooctanone and 2-hydroxycyclododecanone with 1,3-propanediol gave the corresponding bicyclic dihydro-1,4-dioxepins as sole products.From 2-hydroxycyclohexanone and 1,3-propanedithiol the corresponding bicyclic dihydro-1,4-dithiepin was obtained.In some cases the reaction gave rise to mixtures of isomeric products.A general mechanism for the reaction is proposed.
GENERAL APPROACH FOR THE SYNTHESIS OF POLYQUINANES. FACILE GENERATION OF MOLECULAR COMPLEXITY VIA REACTION OF 1,2-DICARBONYL COMPOUNDS WITH DIMETHYL 3-KETOGLUTARATE
Mitschka, R.,Oehldrich, J.,Takahashi, K.,Cook, J. M.,Weiss, U.,Silverton, J. V.
, p. 4521 - 4542 (2007/10/02)
The condensation of dimethyl 3-ketoglutarate 1 with 1,2-dicarbonyl compounds provides access to the polyquinane derivatives tricyclo1,5>undecane-3,7,9-trione 27, tricyclo1,5>undecane 31; tetracyclo4,13.010,13>-tridecane-2,6,8,12-tetraone 41; tetracyclo1,5.08,12>tetradecane-2,7,9,14-tetraone 44; and the tetracyclo10,13>tridecane triones 5b and 6b.The unique structure of staurane tetraone 41 has resulted in spontaneous resolution of the two antipodes on crystallization from DMF.In addition, examination of the crystal structures of tetraones 41 and 44, in terms of strain energy, coupled with the steric accessibility of the β-diketone functionality contained in 41 and 44 have been employed to explain why tetraone 44 and trione 27 undergo a retro-Claisen reaction (CH3OH) more rapidly than staurane tetraone 41.
