114827-53-1

Basic information

• Product Name: erythro-1-phenylethyl 2-pyridyl sulfoxide
• Synonyms: erythro-1-phenylethyl 2-pyridyl sulfoxide
• CAS NO: 114827-53-1
• Molecular Weight: 231.318
• Mol File: 114827-53-1.mol

Chemical Properties

• CAS DataBase Reference: erythro-1-phenylethyl 2-pyridyl sulfoxide(CAS DataBase Reference)
• NIST Chemistry Reference: erythro-1-phenylethyl 2-pyridyl sulfoxide(114827-53-1)
• EPA Substance Registry System: erythro-1-phenylethyl 2-pyridyl sulfoxide(114827-53-1)

Safety Data

• Hazardous Substances Data: 114827-53-1(Hazardous Substances Data)

Upstream product

• 58086-68-3 1-Phenylethyl 2-pyridyl sulfide 
• 585-71-7 (1-bromoethyl)benzne 
• 89818-49-5 (S-)-(-) 1-phenylethyl 2-pyridyl sulfide 
• 89818-50-8 (+)-(R)-1-Phenyl ethyl 2-pyridyl sulfide 

Downstream Products

• 89818-51-9 (+)-(S)-2-(1-methylbenzyl)pyridine 
• 89818-52-0 (R)-(-)-2-(1-phenylethyl)pyridine 
• 101-82-6 2-Benzylpyridine 
• 14159-54-7 2-(1-phenylethyl)pyridine 
• 112498-17-6 1-Methyl-2-((R)-1-phenyl-ethyl)-pyridinium; iodide 

Relevant articles and documents

Ligand Coupling within ?-Sulphurane Intermediates formed in the Reaction of Benzyl 2-Pyridyl and Related Sulphoxides with Grignard reagents

The reaction of benzyl or 1-phenylethyl 2-pyridyl sulphoxide (1) or (18) with a Grignard reagent was found to give the ligand-coupling product, i.e., 2-benzylpyridine or 2-(1-phenylethyl)pyridine (2) or (22) in excellent yield.This coupling reaction was found to proceed whithin the ?-sulphurane formed as an intermediate upon treatment of benzyl 2-pyridyl and related sulphoxides with a Grignard reagent.The stereochemical course of this coupling reaction involves complete retention at the benzylic carbon.

Some Studies on syn-Elimination Reactions

On heating to 220 deg C the 2-alkylthiopyridine N-oxide (6) was found to undergo syn-elimination giving ethyl acrylate.Sulphoxide (15) was more prone to syn-elimination than sulphoxide (16) demonstrating the importance of β-hydrogen acidity in the rate of sulphoxide syn-eliminations.

LIGAND COUPLING THROUGH ?-SULFURANE --- COMPLETE RETENTION OF CONFIGURATION OF 1-PHENYLETHYL GROUP IN THE REACTION OF 1-PHENYLETHYL 2-PYRIDYL SULFOXIDE WITH GRIGNARD REAGENT

The reaction of benzyl or 1-phenylethyl 2-pyridyl sulfoxide with Grignard reagent proceeds via a ?-sulfurane as an intermediate to give the coupling product, 2-benzylpyridine or 2-(1-phenylethyl)pyridine in quantitative yield.Stereochemistry for this reaction is complete retention at the benzylic carbon atom.