3657-08-7

Usage

InChI:InChI=1/C15H22N4O4/c1-3-5-7-12(8-6-4-2)16-17-14-10-9-13(18(20)21)11-15(14)19(22)23/h9-11,17H,3-8H2,1-2H3

Upstream product

• 409321-22-8 nonan-5-one-hydrazone 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 623-93-8 5-nonanol 
• 502-56-7 nonanone-5 
• 105494-88-0 5-nonyl phenyl sulfone 
• 56651-45-7 Di-n-butylketon-diphenyl-dithioacetal 
• 56651-44-6 1,1-bis-phenylsulfanyl-pentane 
• 34009-04-6 phenyl pentyl sulfone 
• 1129-70-0 pentyl phenyl sulfide 
• 119-26-6 (2,4-dinitro-phenyl)-hydrazine 
• 105494-80-2 1-phenylthio-1-tributylstannyl-1-trimethylsilylpentane 
• 91787-42-7 5-phenylsulphonyl-5-trimethylsilylnonane 
• 91787-36-9 1-phenylsulphonyl-1-trimethylsilylpentane 
• 91787-45-0 5-phenylthio-5-trimethylsilylnonane 

Relevant academic research and scientific papers

Kinetics and mechanism of oxidation of aliphatic secondary alcohols by benzyltrimethylammonium chlorobromate

Oxidation of several secondary alcohols by benzyltrimethylammonium chlorobromate (BTMACB) in aqueous acetic acid leads to the formation of corresponding ketones. The reaction is first order with respect to BTMACB and the alcohols. The reaction failed to induce the polymerization of acrylonitrile. There is no effect of tetrabutylammonium chloride on the reaction rate. The proposed reactive oxidizing species is chlorobromate ion. The oxidation of benzhydrol-α-d (PhCDOHPh) exhibited a substantial primary kinetic isotope effect (kH/kD = 5.61 at 298 K). The effect of solvent composition indicated that the rate increases with an increase in the polarity of the solvent. The reaction is susceptible to both the polar and steric effects of the substituents. A mechanism involving transfer of a hydride ion in the ratedetermining step has been proposed.

The Synthesis of Ketones via α-Silyl Sulphides

α-Phenylthiosilanes (2) have been prepared by alkylation of the anion (4) derived from the 1-phenylthio-1-trimethylsilylalkane (1).These anions (4) have benn prepared by a variety of methods including, direct deprotonation of (1), displacement of a phenylthio group by lithium naphthalenide addition of an alkyl-lithium to 1-phenylthio-1-trimethylsilylethene (7), and transmetallation of a tributylstannyl moiety.The formation of an alkyl-lithium by reaction of lithium naphthalenide with a phenyl sulphide provided an additional route to (2) from bis(phenylthio)acetals (8).An alternative path to the α-phenylthiosilanes (2) was to reduce the corresponding α-phenylsulphonylsilane (15); these, in turn, being readily available from alkylation or silylation of α-sulphonyl anions.The α-phenylthiosilanes (2) were converted into the O-trimethylsilylphenylthioacetal (18) by the sila-Pummerer rearrangement, although this was complicated by vinyl sulphide (20) formation in certain cases.Subsequent hydrolysis of (18) and (20) gave the ketone (3).

Synthesis of Alkenes via Peterson Reaction

The α-phenylthiosilanes (2) have been used to prepare the α-silyl anions (1) by reaction with lithium naphthalenide; subsequent condensation with a carbonyl compound gave the alkene (8) via the Peterson reaction.The α-phenylthiosilanes (2) were prepared from n,n-bis(phenylthio)acetals (4) by reaction with lithium naphthalenide and chlorotrimethylsilane.The n,n-bis(phenylthio)acetals (4) were obtained, in turn, from 1,1-bis(phenylthio)acetals (5) by anion formation with butyl-lithium-N,N,N',N'-tetramethylethylenediamine complex in hexane followed by reaction with an alkyl halide.The Peterson reaction was also used to prepare vinyl sulphides (9) and vinyl sulphones (13).