10269-15-5

Upstream product

• 75-84-3 2,2-dimethyl-propanol-1 
• 930-69-8 sodium thiophenolate 
• 931-59-9 benzenesulfenyl chloride 
• 16427-42-2 methanesulfonic acid 2,2-dimethyl-propyl ester 
• 108-98-5 thiophenol 
• 27767-51-7 4r-Chlor-3c-phenylmercapto-2,2-dimethyl-buten-⁽³⁾ 
• 27767-52-8 2-tert-butyl-2-phenylthiovinyl chloride 
• 33974-41-3 neopentylmagnesium bromide 
• 1859-03-6 ethyl benzenesulfinate 
• 2346-07-8 neopentyl tosylate 
• 7210-80-2 neopentyl phenyl sulphide 
• 27767-53-9 4r-Chlor-3t-phenylsulfon-2,2-dimethyl-buten-⁽³⁾ 
• 27767-54-0 4r-Chlor-3c-phenylsulfon-2,2-dimethyl-buten-⁽³⁾ 
• 10335-98-5 neopentyl phenyl sulfoxide 

Relevant academic research and scientific papers

Alkylation of Nitropyridines via Vicarious Nucleophilic Substitution

Electrophilic nitropyridines react with sulfonyl-stabilized carbanions to give products of C-H alkylation via vicarious nucleophilic substitution. The process consists of formation of the Meisenheimer-type adduct followed by base-induced β-elimination of the sulfinic acid (e.g., PhSO2H). Mechanistic studies reveal that in the latter step alkyl substituent and adjacent nitro group tend to planarize for effective stabilization of benzyl anion, and thus, adduct of hindered isopropyl carbanion remains stable toward elimination for steric reasons.

Sulfoxide and Sulfone Synthesis via Electrochemical Oxidation of Sulfides

The oxidation of diaryl sulfides and aryl alkyl sulfides to the corresponding sulfoxides and sulfones under electrochemical conditions is reported. Sulfoxides are selectively obtained in good yield under a constant current of 5 mA for 10 h in DMF, while sulfones are formed as the major product under a constant current of 10 or 20 mA for 10 h in MeOH. The oxygen of both the sulfoxide and sulfone function is derived from water.

ELIMINATION AND ADDITION REACTIONS. PART 39. VARIATION OF NUCLEOFUGALITY WITH TRANSITION STATE STRUCTURE-1,3- AND 1,2-ELIMINATIONS FROM CARBANIONS COMPARED.

Phenylsulphonyl-activated 1,3-eliminations have been investigated with the objective of determining nucleofugalities of six leaving groups.In cyclohexane-1,3-diyl and propane-1,3-diyl system unactivated 1,2-elimination of 'poor' leaving groups occurs faster than 1,3-elimination.In 2,2-dimethylpropane-1,3-diyl substrates, however, quantitative 1,3-eliminations occur and the nucleofugalities of Br, Cl, OTs, PhSO2, PhS, PhO, have been determined.In a linear free energy relationship extending over 15 pKa units and 12 rank units, an excellent correlation of nucleofugality with the pKa of the conjugate acid of the leaving group is found.It is concluded from the comparison with 1,2-eliminations previously studied that 1,3-elimination involves considerable leaving group separation and ring formation in the transition state.With bromide as leaving group, the 2,2-dimethylpropane-1,3-diyl system is 1000 times more reactive in cyclopropane formation than the propane-1,3-diyl system; this is the first quantitation of the Thorpe-Ingold effect in homocyclic ring formation.With chloride and tosylate leaving groups, smaller accelerations are observed.