79893-70-2

Upstream product

• 33735-95-4 9-[bromo-(phenyl)methylene]-9H-fluorene 
• 79893-69-9 9-(α-azidobenzyliden)fluoren 
• 64874-48-2 3'-phenylspirooxathiazole> 5'-oxide 
• 1141-08-8 4,4'-dimethylthiobenzophenone 
• 67-56-1 methanol 
• 1836-87-9 9-Benzylidene-9H-fluorene 
• 79898-41-2 9-bromo-9-[bromo-(phenyl)methyl]-9H-fluorene 

Downstream Products

• 97759-35-8 C₃₅H₂₇NOS 
• 97745-99-8 C₃₃H₂₃NOS 
• 88073-42-1 2',2'-di-p-tolyl-4'-phenylspirothiazole> 
• 1341189-56-7 (3',6'-diphenylspiro[fluorene-9,2'-[1,4]oxazine]-5'-yl)-(phenyl)methanone 
• 1341189-54-5 4'-benzoyl-2',4'-diphenylspiro[fluorene-9,3'-pyrrol]-5'(4'H)-one 
• 1431934-91-6 ethyl 6′-methyl-3′-phenyl-2H′,9′H-spiro[fluorene-2,9′-[1,4]-oxazine]-5′-carboxylate 
• 1431934-99-4 ethyl 2-[fluoren-9-ylidene(phenyl)methylimino]-3-oxobutanoate 
• 1431935-00-0 ethyl 2-[fluoren-9-ylidene(phenyl)methylimino]-3-oxo-3-phenylpropanoate 
• 1431934-92-7 ethyl 3′,6′-diphenyl-2H′,9′H-spiro[fluorene-2,9′-[1,4]-oxazine]-5′-carboxylate 
• 1431934-93-8 ethyl 3′-phenyl-6′-trifluoromethyl-2H′,9′H-spiro[fluorene-2,9′-[1,4]-oxazine]-5′-carboxylate 

Relevant academic research and scientific papers

Thermal Fragmentation of a 1,5,2-Oxathiazole 5-Oxide system via Two Parallel Pathways: Interception of a Vinyl Nitrene and of a Sulphene

Heating of 1,5,2-oxathiazole 5-oxide (2) (obtained by cycloaddition of fluorene-9-thione S-oxide and benzonitrile oxide) in benzene resulted in the formation of the dispirothiazole-5',9"-fluorene> 1',1'-dioxide (3) (84percent).The formation of product (3) is explained by assuming thermal fragmentation of (2) via two parallel pathways, one involving the loss of benzonitrile to give fluorene-9-thione S,S-dioxide (5) and the other the elimination of sulphur dioxide to produce the vinyl nitrene (7).Cycloaddition of the sulphene (5) and the nitrene (7) then leads to the heterocycle (3).This mechanism is supported by the fact that the vinyl nitrene (7) could be trapped by reaction with 4,4'-dimethylthiobenzophenone, and the sulphene (5) by reaction with methanol.The alternative rationale for the formation of (3), viz. reaction of an azirine (4) with the sulphene (5), could be ruled out.

Von der basenkatalysierten Ringoeffnung von 2H-Azirinen zu einer α-Alkylierungsmethode von primaeren Aminen

It is shown than fluorene-9'-spiro-2-(3-phenyl-2H-azirine) (1) on treatment with various alcohols in the presence of the corresponding alkoxide ions yields N-(9'-fluorenyl)benzimidates 2a-d (Scheme 1). 2,2,3-Triphenyl-2H-aziridine (3) reacts with methanol in a similar manner (Scheme 2).Benzimidates 2a (Scheme 3), 8 (Scheme 4) and 10 (Scheme 5) can easily be deprotonated by butyllithium (BuLi) or lithium diisopropylamide (LDA) in tetrahydrofuran (THF) to 1-methoxy-2-aza-allylanions, that can be alkylated, at C(3), exclusively, by various electrophiles (e.g.R-X (X = I, Br), RCHO or methyl acrylate (see also Scheme 6)).As the acidic hydrolyses (1 N HCl) of benzimidates 9 and 11 leads to the corresponding α-alkylated free amines 15 and 18 (Scheme 7 and 8), benzoyl derivatives 16 and 19 are obtained from the hydrolysis under basic conditions.On the other hand it is observed that a catalyzed Chapman rearrangement of 9 and 11 results in the formation of N-benzoyl-N-methyl derivatives 17 and 20 (Scheme 7 and 8).The described reactions offer a simple method for the α-alkylation of actived primary amines.