4440-32-8

Basic information

• Product Name: 9H-Fluorene-9-thione,S-oxide
• CAS NO: 4440-32-8
• Molecular Weight: 212.272
• Mol File: 4440-32-8.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 9H-Fluorene-9-thione,S-oxide (CAS DataBase Reference)
• NIST Chemistry Reference: 9H-Fluorene-9-thione,S-oxide (4440-32-8)
• EPA Substance Registry System: 9H-Fluorene-9-thione,S-oxide (4440-32-8)

Safety Data

• Hazardous Substances Data: 4440-32-8(Hazardous Substances Data)

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 86-73-7 9H-fluorene 
• 132020-45-2 di-9-fluorenyl sulfoxide 
• 106864-89-5 methyl 9-fluorenesulfinate 
• 76256-16-1 2'-methyl-3'-phenylfluorene-9-spiro-4'-(1',2'-thiazolidine)-5'-spiro-9-fluorene 1'-oxide 
• 79310-05-7 3',6'-dihydro-3',5',6'-triphenylspiro(fluorene-9,2'-<1,3,4>thiadiazine) 1'-oxide 
• 830-72-8 9H-fluorene-9-thione 
• 1141-08-8 4,4'-dimethylthiobenzophenone 
• 197901-71-6 9-fluorenyl trichloromethyl sulfoxide 

Downstream Products

• 64874-48-2 3'-phenylspirooxathiazole> 5'-oxide 
• 76256-17-2 3'-methyl-4'-phenylfluorene-9-spiro-2'-(1',3'-thiazolidine)-5'-spiro-9-fluorene 1'-oxide 
• 64874-49-3 3'-phenyl-spiro[fluorene-9,5'-[1,4,2]oxathiazole] 4'-oxide 
• 50999-08-1 3',5'-diphenyl-3'H-spiro[fluorene-9,2'-[1,3,4]thiadiazole] 1'-oxide 
• 79310-09-1 2',3',5',6',7',8'-hexahydro-2'-phenyl-6'-t-butylspiro(fluorene-9,3'-<4,1,2>benzothiadiazine) 4'-oxide 
• 79310-10-4 4',4a',5',6',7',8'-hexahydro-2'-phenyl-6'-t-butylspiro(fluorene-9,4'-<3,1,2>benzothiadiazine) 3'-oxide 
• 79310-05-7 3',6'-dihydro-3',5',6'-triphenylspiro(fluorene-9,2'-<1,3,4>thiadiazine) 1'-oxide 
• 79310-06-8 trans-2',5'-dihydro-2',4',5'-triphenylspiro(fluorene-9,6'-<1,2,3>thiadiazine) 1'-oxide 
• 79310-06-8 cis-2',5'-dihydro-2',4',5'-triphenylspiro(fluorene-9,6'-<1,2,3>thiadiazine) 1'-oxide 
• 746-47-4 tetrabenzo[5.5]fulvalene 
• 486-25-9 9-fluorenone 
• 6596-81-2 1,3-dimethylimidazole-2-thione 
• 4427-65-0 1,2,3,4,5,6,8,9,10,11,12,13-dodecahydrodicycloocta[1,4]dithiin 
• 50999-12-7 3',5'-diphenyl-3'H-spiro[fluorene-9,2'-[1,3,4]thiadiazole] 1',1'-dioxide 

Relevant articles and documents

Study of Reactions Leading to Sulfine Formation. 6. Base-Catalyzed Decomposition of Di-9-fluorenyl Sulfoxide

When treated with CH3ONa in CH3OH-CH2Cl2, di-9-fluorenyl sulfoxide (3) undergoes elimination readily to afford 9-thiofluorenone S-oxide (4) and fluorene (eq 2).Comparison of the rate of the elimination to the rate of disappearance in the presence of CD3OD of the 1H NMR signal for the 9-H in 3 shows that the mechanism of this sulfine-forming elimination is (E1cB)rev, the rate of cleavage of the intermediate α-sulfinyl carbanion 7 to give 4 and a 9-fluorenyl carbanion being over 100 times slower than the rate at which 7 is protonated to regenerate 3.The (E1cB)rev behavior of this elimination is contrasted with the (E1cB)rev/(E1cB)irrev borderline behavior of the elimination of diarylmethyl (arylmethyl)sulfonyl sulfoxides 1, and a reason for this at first sight unexpected difference in behavior is presented.

Rates of H/D Exchange of 9-Fluorenyl Sulfoxides: Evidence for an Irreversible E1cB Mechanism for Base-Induced Sulfine Formation from Methyl Diarylmethanesulfinates

A previous study had shown that the base-catalyzed, sulfine-forming eliminations of methyl 9-fluorenesulfinate (4) and other methyl diarylmethanesulfinates take place by either an E1cB-irreversible or an E2 mechanism, rather than the E1cB-reversible mechanism that had been expected.In the present work the rates (kexch) of DABCO (diazacyclooctane)-catalyzed H/D exchange of the 9-H in a series of 9-fluorenyl sulfoxides (3) have been determined at 25 deg C in CD3OD.From a plot of log kexch vs ?* for R in 3 the anticipated rate for the DABCO-catalyzed formation ofthe 9-fluorenyl carbanion from 4 (eq 3, R = OCH3) can be estimated.Comparison of this rate with the actual rate (kelim) of the DABCO-catalyzed, sulfine-forming elimination of 4 (eq 5) indicates that the elimination does not take place by an E2 mechanism in which there is a significant degree of cleavage of the S(O)-OCH3 bond in the rate-determining transition state.The results are, however, entirely consistent with an E1cB-irreversible mechanism for the elimination.

Preparation of sulfines by alkylidenation of sulfur dioxide using α-silyl carbanions

The synthesis of sulfines 4 from a series of active methylene compounds is described.Deprotonation, followed by silylation, gives the trimethylsilyl compounds 2.Subsequent deprotonation to α-silyl carbanions and treatment with an excess of sulfur dioxide