73651-50-0

Usage

InChI:InChI=1/C5H8Cl2O/c1-3-4(8)5(2,6)7/h3H2,1-2H3

Upstream product

• 78102-51-9 trans-2,3-Dichlor-2-ethyl-3-methyloxiran 
• 96-22-0 pentan-3-one 

Relevant academic research and scientific papers

A Novel Configuration-Controlled Stereoselectivity in Enol Silylation of Ketones. Stereochemistry of Amine-Promoted Enol Silylation of Meso and Racemic α,α'-Dichloro Ketones and of Ketonization of the Resultant Enol Silyl Ethers

Stereochemistry in amine-promoted enol trimethylsilylation of meso- and dl-α,α'-dichloro ketones, RCHClCOCHClR (1a; R=Me and 1b; R=i-Pr), and in ketonization of the resultant enol silyl ethers (2a and 2b) has been studied.The Et3N-promoted silylation of 1 in benzene shows a marked diastereoselectivity; the racemic isomer exhibits 84percent and 98percent (E)-selectivities for 1a and 1b, while the meso isomer, 97percent and 98percent (Z)-selectivities respectively.Both stereo- and diastereo-selectivities markedly depend upon solvent polarity and base strength.For example, both meso- and dl-1a showed small (Z)-selectivities in DMF.The diastereoselectivity markedly decreased with increasing base strength; both 1a and 1b exclusively gave the (E)-isomer of 2 irrespective of the configuration of the ketone when treated with lithium diisopropylamide in the presence of chlorotrimethylsilane at -78 deg C.The ketonization of 2a and 2b was also diastereoselective in the direction opposite that observed in the forward reaction; the (E)-isomer predominantly gave the meso ketone (24percent d.e.), while the (Z)-isomer, the racemic ketone (ca. 70percent d.e.) upon protonation with concd. hydrochloric acid in THF.

Halogen Epoxides, 3. Reactions of 2-Chloro- and 2,3-Dichlorooxiranes with Silver Tetrafluoroborate: Synthesis of α-Fluorinated Carbonyl Compounds

Reactions of chlorinated oxiranes with silver tetrafluoroborate in ether have been investigated.Substituted-2-chlorooxiranes (4a - e) afforded the corresponding α-fluorocarbonyl compounds (7a - e) as major products and the isomeric α-chlorocarbonyl compounds (8a - e) as minor products.Substituted 2,3-dichlorooxiranes (10, 14, 20, 24) yielded the isomeric α,α-dichloroketones (13, 19, 22, 26b, 29b) as well as the corresponding α-chloro-α-fluoroketones (12, 17, 21, 26a, 29a) and α,β-unsaturated α-chloroketones (18, 23, 27, 30).The course of the reaction was rationalized.Similar reaction with α-chloroketones and with α,α-dichloroketones succeeded only at substrates (8b, 35) in which the chlorine substituents were in benzylic positions.