38328-17-5

Upstream product

• 121239-03-0 3,3-diphenyl-1-penten-4-one 
• 778-66-5 1,1-diphenyl-1-propene 
• 74-88-4 methyl iodide 
• 2575-20-4 3,3-diphenylbutan-2-one 
• 22875-81-6 3,3-diphenyl-butan-2-ol 
• 121239-05-2 3,3-diphenyl-5-phenylsulfinyl 
• 781-35-1 1,1-diphenylacetone 
• 79238-95-2 2,3-diphenyl-4-trimethylsilylbutan-2-ol 

Downstream Products

• 110530-92-2 butyl-(3,3-diphenyl-butyl)-sulfide 
• 5223-61-0 2,2-diphenyl-butane 
• 101441-39-8 1,1,1-Trichlor-3,4-diphenyl-penten-⁽⁴⁾ 
• 22875-82-7 2,2-diphenylpropanal 

Relevant academic research and scientific papers

Carbonium Ion Rearrangements Controlled by the Presence of a Silyl Group

γ-Silyl tertiary alcohols rearrange in protic acid with 1,2-shift of hydride, phenyl, or alkyl groups, and loss of the silyl group to give alkenes.The placing of the silyl group thus controls the carbonium ion rearrangement in a preparatively useful way.Methoxycarbonyl groups do not migrate; instead, cyclopropanes are formed, except when the conformation suitable for cyclopropane formation is unattainable.When the alkene product is 2,2-disubstituted, it can be reprotonated under the reaction conditions and does not therefore always survive.This can be avoided by carrying out the reaction using a Lewis acid on the silyl ether.The starting γ-silyl alcohols are prepared by a variety of versatile methods.

Photochemistry of two diphenyl β,γ-enones and a series of methyl- and phenyl-substituted α-phenyl ketones

The photochemistry of the diphenyl β,γ-enones 2 and 3 and the methyl- and phenyl-substituted α-phenyl ketones 4-9 has been studied, using mainly benzene as solvent.Irradation of 2 with λ 300 nm leads to the 1,3-acyl shift (1,3-AS) product 17, relatively small amounts of the decarbonylation products 15 and 16, and the photo-oxidation products benzophenone (18) and the α,β-unsaturated aldehyde 19.Direct irradation of the 1,3-AS product 17 yields 15, 16, 18 and 19, but no 2.Direct irradation of 3 with λ 350 nm leads mainly to the formation of 1,3-AS products (E)- and (Z)-22, the decarbonylation products (E)- and (Z)-20 and 21 and, in addition, a small amount of the cis-di-?-methane isomer 23.Direct irradation of the substituted α-phenyl ketones 4, 5, 8 and 9 with λ 300 nm leads predominantly to the formation of the radical coupling products 2,3-butanedione and 24-27, respectively, whereas 6 and 7 yield 1,2-diphenyl-1,2-ethanedione and the respective 24 and 25.The acetone-sensitized irradation of 4 leads to 4-phenyl-2-butanone (33) in addition to 2,3-butanedione and 1,2-diphenylethane (24).

CARBONIUM ION REARRANGEMENTS CONTROLLED BY THE PRESENCE OF A SILYL GROUP

Tertiary alcohols with a γ-silyl group (3) generally undergo a simple carbonium ion rearrangement in acid giving a single alkene product (4) with loss of the silyl group.

Some uses of silicon compounds in organic synthesis

1.The amount of γ-phenylthioalkylation of silyl dienol ethers is increased when the triphenylsilyl ether is used in place of the trimethylsilyl ether.Phenylthiomethylation is the least γ-selective carbon electrophile of several tried so far. 2.The acid-catalysed reactions of a range of γ-silyl tertiary alcohols cleanly give rearrangement, in which the silyl group controls the outcome.The reactions are similar in several respects to the rearrangements of the corresponding pinacols, except that the silicon controlled reactions are usually cleaner and give higher yields.The reaction is particularly useful for setting up quaternary carbon atoms.