33226-81-2

Upstream product

• 60734-27-2 N-(9H-fluoren-9-ylidene)methanamine 
• 3376-23-6 C-phenyl-N-methylnitrone 
• 830-72-8 9H-fluorene-9-thione 

Downstream Products

• 39656-24-1 3'-methyl-4',4'-diphenylfluorene-9-spiro-2'-oxazolidin-5'-one 
• 21086-24-8 2,4-bis(diphenylmethylene)-cyclobutane-1,3-dione 
• 55832-70-7 C₂₂H₂₃NO₃ 
• 104202-27-9 2,4-dipropan-2-ylidene-5-fluoren-9-ylimino-1,3-dioxolane 
• 104202-31-5 2,4-difluoren-9-ylidenecyclobutane-1,3-dione 
• 55832-69-4 3',4',4'-trimethylfluorene-9-spiro-2'-oxazolidin-5'-one 
• 139286-66-1 spiro 
• 71422-13-4 1'-methyl-5',5'-diphenyl-spiro[fluorene-9,2'-pyrrolidine]-3'r,4'c-dicarboxylic acid anhydride 
• 139286-80-9 Ethyl 2-benzoyl-(9-fluorenyliden)acetate 
• 2157-52-0 9-fluorenone oxime 
• 78394-35-1 2'-methyl-4'-phenylfluorene-9-spiro-3'-<1,2,4>oxadiazolidin-5'-one 

Relevant academic research and scientific papers

Imines and Derivatives. Part 24. Nitrone Synthesis by Imine Oxidation using either a Peroxyacid or Dimethyldioxirane

The oxidation of N-alkyl imines by m-chloroperoxybenzoic acid to yield nitrones was facilitated by (i) the presence of C-aryl substituents, (ii) steric inhibition of attack at the imino C-atom, (iii) electron donating para-substituents on the C-aryl substituent, (iv) non-hydroxylic solvents, (v) optimal conjugation between C-aryl substituents and the imino group, and (vi) less bulky N-alkyl groups. The oxidation of N-alkyl imines by dimethyldioxirane (DMD) in dichloromethane-acetone solution yielded nitrones without evidence of oxaziridine formation.The yields of isolated nitrones were higher for C,C-diaryl imines and for imines bearing less bulky N-alkyl substituents.N-H substituted ketimines were found to yield oximes after reaction with dimethyldioxirane.

CYCLO-ADDITION REACTIONS OF THIOFLUORENONE WITH NITRONES

Thiofluorenone reacts with C-phenyl-N-methylnitrone to give, initially, a 1,2,5-oxathiazolidine.Spontaneous loss of sulphur monoxide then produces a dipolar species which reacts with a second molecule of thiofluorenone to give a 1,2-thiazolidine.This thiazolidine partially isomerizes to a 1,3-thiazolidine on heating.The corresponding 1,2-thiazolidine 1-oxide similarly undergoes a cycloreversion-recyclization reaction to the isomeric 1,3-thiazolidine 1-oxide.The reaction of thiofluorenone with C-phenyl-N-phenylnitrone gives a 1,2-thiazetidine 1-oxide, a benzothiazine S-oxide, and a thiazolidine.The formation of the first two products can be explained by involving a rearrangement of the primary 1:1 adduct; the last product may derive from the same adduct by loss of sulphur monoxide followed by a reaction with a second molecule of thione.