80423-31-0

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 532-27-4 1-chloroacetophenone 
• 7449-74-3 N-methyl-N-trimethylsilylacetamide 
• 2648-61-5 2,2-dichloroacetophenone 
• 78279-92-2 2,3,5,6-tetramethyl-1,4-bis(trimethylsilyl)-1,4-diaza-2,5-cyclo-hexadiene 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 
• 54034-90-1 1,1,1-trichloro-2-phenyl-2-(trimethylsiloxy)ethane 

Downstream Products

• 101-41-7 benzeneacetic acid methyl ester 
• 91873-55-1 chloro-2 phenyl-1 hexanedione-1,5 
• 91873-56-2 chloro-2 diphenyl-1,5 pentanedione-1,5 
• 103-82-2 phenylacetic acid 
• 80423-30-9 (E)-2-chloro-1-phenyl-1-(trimethylsilyloxy)ethylene 
• 532-27-4 1-chloroacetophenone 
• 1404225-07-5 methyl (R)-3-chloro-5-oxo-2-phenylcyclopent-1-enecarboxylate 
• 64390-04-1 trans 1-(2-benzoylcyclopropyl)ethanone 
• 3238-03-7 (2-benzoylcyclopropyl)(phenyl)methanone 
• 91-48-5 (E)-2,3-diphenylpropenoic acid 
• 7465-32-9 3-phenyl-1-oxaspiro[3.5]nonan-2-one 

Relevant academic research and scientific papers

Organosilicon Reducing Reagents for Stereoselective Formations of Silyl Enol Ethers from α-Halo Carbonyl Compounds

Salt-free stereoselective synthesis of silyl enol ethers was achieved by treating α-halo carbonyl compounds with 2,3,5,6-tetramethyl-1,4-bis(trimethylsilyl)-1,4-dihydropyrazine. In this reaction, easily removable trimethylsilyl halides and 2,3,5,6-tetramethylpyrazine were generated as the reaction byproducts. Due to the inertness of the reaction byproducts, we found a one-pot transformation of the in situ generated silyl enol ethers into various α-functionalized carbonyls by reaction with Togni-II reagent or aldehydes.

A Solvent-Free Reaction for Silyl Enol Ethers Synthesis

Silyl enol ethers are extremely useful nucleophilic intermediates for chemical transformations because they are synthetically versatile substrates for a wide range of C-C bond-forming reactions. Here, we present a new, mild, and solvent-free procedure for the synthesis of silyl enol ethers that employs a catalytic amount of solid-supported base and an equimolar amount of N, O -(bistrimethylsilyl)acetamide as a silylating agent.

METHOD FOR PRODUCING SILYLENOL ETHERS

The present invention provides a method for producing a silyl enol ether compound, which is convenient, has highly broad utility and places a low environmental load (less waste). The present invention relates to a method for producing silyl enol ether compound (3), including reacting ketone or aldehyde compound (1) with allylsilane compound (2) in the presence of a base and 0.00001 to 0.5 equivalents of an acid catalyst relative to ketone or aldehyde compound (1), wherein R1 is a hydrogen atom, an alkyl group, an aryl group or the like; R2 and R3 are each a hydrogen atom, a halogen atom, an alkyl group, an aryl group or the like; R1 and R3, R1 and R2, or R2 and R3 optionally form a ring, together with the carbon atom(s) bonded thereto; R4 , R5 and R6 are each a hydrogen atom, an alkyl group or the like; two of R4, R5 and R6 optionally form a ring; R7, R8, R9, R10 and R11 are each a hydrogen atom, an alkyl group or the like; two of R7, R8, R9, R10 and R11 optionally form a ring.

1,2-H shift in copper-chlorocarbenoid intermediate during CuCl/bpy-promoted stereoselective dechlorination of 2,2,2-trichloroethyl alkyl ethers to (Z)-1-alkoxy-2-chloroethenes

(Chemical Equation Presented) Reaction of 2,2,2-trichloroethyl alkyl ethers with 2 molar equiv of CuCl/bpy in refluxing DCE yielded (Z)-1-alkoxy-2- chloroethenes stereoselectively as the major product via 1,2-H shift in copper-chlorocarbenoid intermediate. 2,2,2-Trichloroethyl carboxylates undergo a radical 1,2-acyloxy shift under similar conditions.

Silazanes/catalytic bases: Mild, powerful and chemoselective agents for the preparation of enol silyl ethers from ketones and aldehydes

We have developed an efficient method for the preparation of enol silyl ethers using novel agents, silazanes together with NaH or DBU catalyst, wherein TMS and TBDMS groups were smoothly and chemoselectively introduced into ketones and aldehydes under mil

A CONVENIENT PREPARATION METHOD OF THE VINYLIC HALIDE ISOMER OF CHLOROTRIMETHYLSILYL ENOL ETHERS

Reaction of trimethylsilyliodide (generated in situ from trimethylsilylchloride and sodium iodide) in the presence of triethylamine in acetonitrile with α-chloroketones yields the vinylic halide isomer of chlorotrimethylsilyl enol ethers.

Generation of 2-(Trimethylsiloxy)allyl Cations and Their Reactions with 1,3-Dienes. Change in Mechanism of 3 + 4 -> 7 Cycloaddition with Solvent

A series of 12 different 2-(trimethylsiloxy)allyl cations 34a-l is generated from various 2-(trimethylsiloxy)allyl chlorides (3-5) with silver perchlorate.In nitromethane solution, all the cations smoothly react with furan and cyclopentadiene in a 3 + 4 -> 7 manner to give a comprehensive series of 8-oxabicyclooct-6-en-3-ones and bicyclooct-6-en-3-ones in good yields.The cycloaddition with furan proceeds in a stereospecific manner with the retention of allyl cation configurations, in accord with a concerted mechanism.The 3 + 4 -> 7 reactions in THF/ether contrast with those in nitromethane in the following ways. (1) The yield of the adducts strongly depends on the strusture of the allyl cations. (2) The reaction with furan is nonstereospecific. (3) An electrophilic substitution reaction strongly compets with the cycloaddition. (4) The cycloaddition between the cation 34a and 2-methylfuran is highly regioselective (11/12 = 19) as compared to that in nitromethane (the ratio being only 1.9).These findings in THF/ether are reasonably explained by a stepwise mechanism via an intermediate 40.Reactions with acyclic dienes (isoprene and 2,3-dimethylbutadiene), naphthalene, anisole, and methanol are also described.