116233-90-0

Basic information

• Product Name: 2-Thiabicyclo[2.2.1]hept-5-ene, 3-phenyl-
• CAS NO: 116233-90-0
• Molecular Formula: C12H12S
• Molecular Weight: 188.293
• Mol File: 116233-90-0.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 2-Thiabicyclo[2.2.1]hept-5-ene, 3-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Thiabicyclo[2.2.1]hept-5-ene, 3-phenyl-(116233-90-0)
• EPA Substance Registry System: 2-Thiabicyclo[2.2.1]hept-5-ene, 3-phenyl-(116233-90-0)

Safety Data

• Hazardous Substances Data: 116233-90-0(Hazardous Substances Data)

Upstream product

• 2408-88-0 2-benzylsulfanyl-1-phenylethanone 
• 542-92-7 cyclopenta-1,3-diene 
• 104473-83-8 2-phenyl-1,2-benzioselenazol-3(2H)-one selenoxide 
• 100-53-8 phenylmethanethiol 
• 78872-64-7 bis-acetylsulfanyl-phenyl-methane 
• 98909-99-0 [(4-Chloro-phenyldisulfanyl)-phenyl-methyl]-trimethyl-silane 
• 38225-20-6 α-(trimethylsilyl)benzylthiol 
• 100-52-7 benzaldehyde 
• 6725-34-4 thiobenzaldehyde 
• 118201-67-5 3-exo-phenyl-3-endo-trimethylsilyl-2-thiabicyclo<2.2.1>hept-5-ene 

Downstream Products

• 116233-80-8 2-Methyl-4,5-diphenyl-2,5-dihydro-thiazole-2-carboxylic acid methyl ester 
• 116233-78-4 4-Methyl-5-phenyl-2,5-dihydro-thiazole-2-carboxylic acid methyl ester 

Relevant articles and documents

Continuous Flow Synthesis of 2H-Thiopyrans via thia-Diels–Alder Reactions of Photochemically Generated Thioaldehydes

Herein, we report a novel protocol for the photochemical generation of thioaldehydes in a continuous flow process which were in situ reacted with electron rich 1,3-butadienes in thia-Diels–Alder reactions. A broad range of 3,6-dihydro-2H-thiopyrans were formed as products in much higher yields and productivities as compared to classical batch processes. Moreover, greatly reduced reaction times and a facile large-scale preparation of products were achieved by fully exploiting the advantages of continuous flow technology.

STEREOCHEMISTRY OF PROTIODESILYLATION OF 3-TRIMETHYLSILYL-2-THIABICYCLOHEPTENES, HEPTANES AND DERIVATIVES.

Some 3-trimethylsilyl-2-thiabicycloheptenes and heptanes of known configuration were protiodesilylated and the stereochemistry of the reaction was studied.Evidences for a carbanionic intermediate as well as the pivotal role played by the metal coun

Diastereoselectivity in the Diels-Alder Reactions of Thioaldehydes

The Diels-Alder reaction of thioaldehydes with cyclopentadiene occurs with a preference for the endo isomer.The highest selectivity is observed for thioaldehydes RCHS where R is a bulky group such as tert-butyl or isopropyl.Thioaldehydes having α-alkoxy, acetoxy, or siloxy substituents also react with useful endo selectivity.Secondary orbital overlap is a small factor in these reactions since α-oxo thioaldehydes react with relatively low endo selectivity.Steric effects are primarily responsible for the endo preferences observed.The Diels-Alder reactions of chiral α-oxygen substituted thioaldehydes also occur with useful thioformyl face selectivity.A Cornforth transition state 5 is most likely for the selectivity observed for α-alkoxy or acetoxy thioaldehydes, but the α-hydroxy analogue 23 reacts with the opposite facial preference.The highest face selectivity is obtained with the acetonide of thioglyceraldehyde, generated by photolysis of the phenacyl sulfide 15b.