1622-06-6

Upstream product

• 31848-98-3 1-phenyl-5-chloropentan-1-ol 
• 100-52-7 benzaldehyde 
• 211427-69-9 1,3,4,5,6,11a-hexahydro-7E-2-benzothionine 
• 942-93-8 5-Chloro-1-phenyl-1-pentanone 

Relevant academic research and scientific papers

Novel chemical behaviour of a [2,3] sigmatropic rearrangement product of 2-phenyltetrahydrothiopyranium 1-methylide

1,3,4,5,6,11a-Hexahydro-7E-2-benzothionine 5, which is a [2,3] sigmatropic rearrangement product of 2-phenyltetrahydrothiopyranium 1-methylide 8, has been synthesized by reaction of 1-methyl-2-phenyltetrahydrothiopyranium triflate 3 with sodium amide in liquid ammonia or by the fluoride ion-induced desilylation of trans-2-phenyl-1-[(trimethylsilyl)methyl]tetrahydrothiopyranium perchlorate trans-7. Compound 5 is stable at room temperature and reverts to ylide 8 by ring-opening.

Reductive opening of phenyl substituted thiacycloalkanes: New way for sulphur-containing organolithium compounds

The reaction of 2-phenyl substituted four, five and six membered thiacycloalkanes (1, 4 and 7) with lithium and a catalytic amount of DTBB (5 mol %) in THF at -78°C leads to the corresponding sulphur-containing benzylic organolithium compounds (2, 5 and 8), which by reaction with different electrophiles [D2O, Me3SiCl, Bu(t)CHO, Me2CO, Et2CO, (CH2)4CO, CO2] followed by hydrolysis with water afford the expected functionalised mercaptans (3, 6 and 9) in a regioselective manner. Some reaction products (3, 6) are cyclised under acidic conditions (85% phosphoric acid) to yield the corresponding homologous substituted sulphur-containing saturated heterocycles (10, 11).