75548-95-7

Upstream product

• 20399-89-7 (2,6-diphenyl-4H-pyran-4-ylidene)acetaldehyde 
• 80160-61-8 2,6-diphenyl-4-(trimethylsilyl)-4H-thiopyran 
• 3558-68-7 2,6-diphenylpyrylium perchlorate 
• 75548-93-5 4-(formylmethylene)-2,6-diphenyl-4H-thiopyran 
• 55221-37-9 2,6-diphenyl-4-hydroxy-4H-tetrahydrothiopyran 
• 71750-06-6 2,6-diphenyl-2H-thiopyran 
• 57094-07-2 2,6-diphenyl-4H-thiopyran 

Relevant academic research and scientific papers

Synthesis and Reactions of 2,6-Diphenyl-4-(trimethylsilyl)-4H-thiopyran

The title compound 3 was synthesized by trimethylsilyl chloride quenching of 2,6-diphenyl-4-lithio-4H-thiopyran (7), which was obtained by direct lithiation (n-BuLi) of either the 4H-thiopyran 10 or the 2H isomer 6.Compound 6 was readily prepared in one step from the reaction of 2,6-diphenyl-4-hydroxy-4H-thiopyran (5) with NCS in 74percent yield.Compound 3 was metalated to give 12 in 80-85percent yield by using a combination of n-BuLi and t-BuOK in THF at an internal temperature slightly below -20 deg C.The successful reaction of 12 with a variety of ketones and aldehydes provides an alternative synthesis of the Δ4-2,6-diphenyl-4H-thiopyrans 16.The scope and limitation of this Peterson-type reaction of 12 is compared with those of the corresponding Wittig-Horner reagent 2.