54340-70-4Relevant academic research and scientific papers
Transition-Metal-Free Access to Heteroaromatic-Fused 4-Tetralones by the Oxidative Ring Expansion of the Cyclobutanol Moiety
Natho, Philipp,Allen, Lewis A. T.,White, Andrew J. P.,Parsons, Philip J.
, p. 9611 - 9626 (2019/08/16)
Advances in the transition-metal-free cyclobutanol ring expansion to 4-tetralones under N-bromosuccinimide mediation are described. We have expanded the scope of this ring expansion methodology and investigated the effect substituents on the aromatic ring, and the cyclobutanol moiety, have on the outcome of the reaction. Limitations with certain substituents on the cyclobutanol moiety are also described. Further experimental evidence to support our mechanistic understanding is disclosed, and we now preclude the suggested involvement of a primary radical for this transformation.
Regioselective ring opening and isomerization reactions of 3,4-epoxyesters catalyzed by boron trifluoride
Izquierdo, Javier,Rodriguez, Santiago,Gonzalez, Florenci V.
, p. 3856 - 3859 (2011/09/19)
Efficient ring opening of 3,4-epoxyesters with alcohols to produce 4-alkoxy-3-hydroxyesters and their isomerization into 4-ketoesters using boron trifluoride as the catalyst are presented. Both transformations are simple and efficient methods for the synthesis of the above named synthetically useful compounds.
Stereoselective synthesis of 11(E)-tetradecen-1-yl acetate-Sex pheromone of sod webworm (Loxostege sticticalis)
Shakhmaev,Ishbaeva,Shayakhmetova
experimental part, p. 1171 - 1174 (2011/05/04)
On the basic of Claisen rearrangement using orthoesters we carried out stereoselective synthesis of 11(E)-tetradecen-1-yl acetate, a sex pheromone of sod webworm (Loxostege sticticalis), which is a specially dangerous pests of crops.
Pheromones of insects and their analogs. LIV. Synthesis of dodec-9e-en-1-ol and its acetate - Components of the sex pheromone of Sparganothis pilleriana
Odinokov,Vakhidov,Shakhmaev,Zorin
, p. 912 - 914 (2007/10/03)
Using the Claisen rearrangement in the construction of a double bond with the E configuration, we have synthesized dodec-9E-en-1-ol and its acetate, which are components of the sex pheromone of Sparganothis pilleriana.
PREPARATION OF UNSATURATED α,α-DICHLORO ACID CHLORIDES AND INTRAMOLECULAR CYCLOADDITIONS OF THE α-CHLOROKETENES REDUCTIVELY GENERATED FROM THEM. EFFECT OF DOUBLE BOND GEOMETRY ON THE CYCLOADDITION
Snider, Barry B.,Walner, Marleen
, p. 3171 - 3182 (2007/10/02)
Reduction of unsaturated α,α-dichloracid chlorides with zinc dust in THF at reflux generates an unsaturated α-chloroketene which undergoes an intramolecular cycloaddition in good yield.This reaction can be used with three carbon tethers to prepare 5-chlorobicycloheptan-6-ones and 1-chlorobicycloheptan-6-ones but fails with larger tethers.Unsaturated ketenes 18 and 28, with a trans-double bond, react stereospecifically to give bicycloheptanones 21 and 29 in good yield.Unsaturated ketene 12, with a cis-double bond, reacts with loss of stereochemistry to give a 2:1 mixture of 19 and 21 in poor yield.The greater reactivity of trans- than cis-double bonds in intramolecular cycloadditions of ketenes contrasts to intermolecular cycloadditions in which cis-double bonds are more reactive.Adducts 41 and 42 containing both a chlorine and exomethylene group can be prepared readily.Reductive dechlorination of adducts can be achieved with either (n-Bu)3SnH or CrCl2.Ring contraction to give acids 48 and 49 occurs readily on base treatment.
