201789-94-8

Upstream product

• 201789-85-7 4-methyl-3-phenyl-1-penten-3-ol 
• 74752-48-0 4-(3-methyl-2-butenyl)-2-phenyl-Δ²-1,3,4-oxadiazolin-5-one 
• 67-64-1 acetone 
• 56892-26-3 1,1-dimethyl-2-phenyl-1-sila-2-cyclobutene 

Relevant academic research and scientific papers

Stereochemistry of Carbenic 1,2-Vinyl Shifts

Various 1-phenylbut-3-enylidenes, (Ph)CCR2CH=CHR', were generated thermally and photolytically from tosylhydrazone (diazo) precursors. 1,2-Vinyl shifts, leading to 1,3-dienes, R′CH=CHC(Ph)=CR2, were found to predominate over γ-C-H insertion (R = Me) and to compete with 1,2-H shifts (R = H). Intramolecular addition to the double bond was detected in the case of R = R′ = Me. The resulting bicyclobutane is thermally stable and does not mediate the vinyl shift. Stereospecific migration of 1-propenyl groups (R′ = Me), with retention of configuration, was observed on thermolysis and direct photolysis of appropriate substrates. These data exclude the intervention of a triplet diradical and point to vinyl migration in the singlet manifold. Benzophenone-sensitized generation of the carbenes led to partial stereomutation but did not provide conclusive evidence for a triplet rearrangement (isomerization of the diene products could not be avoided under these conditions).

EVIDENCE FOR THE INTERMEDIACY OF 1,1-DIMETHYL-2-PHENYL-1-SILA-1,3-BUTADIENE IN THE PHOTOCHEMISTRY AND PYROLYSIS OF 1,1-DIMETHYL-2-PHENYL-1-SILA-2-CYCLOBUTENE

Photolysis of 1,1-dimethyl-2-phenyl-1-sila-2-cyclobutene (I) in methanol and methanol-O-d1 yields dimethylmethoxy(1-phenyl-2-propenyl)silane and dimethylmethoxy(1-d1-1-phenyl-2-propenyl)silane, respectively, as major products.These products may be formed by reaction of methanol or methanol-O-d1 with 1,1-dimethyl-2-phenyl-1-sila-1,3-butadiene.Gas phase pyrolysis of I and acetone or formaldehyde have also been studied.

Flash Vacuum Pyrolysis of N-Allyl-Substituted 1,3,4-Oxadiazolin-5-ones

The flash vacuum pyrolysis of several N-allyl-substituted 1,3,4-oxadiazolin-5-ones generates nitrile imines which rearrange to diazoalkenes via a 3,3-sigmatropic shift.