14100-81-3

Upstream product

• 291-64-5 cycloheptane 
• 98-08-8 α,α,α-trifluorotoluene 
• 374-74-3 1-chloro-decafluoro-4-trifluoromethyl-cyclohexane 
• 16825-99-3 4-H-decafluoro-1-methyl-1,4-cyclohexadiene 

Downstream Products

• 374-79-8 4-trifluoromethylnonafluorocyclohex-1-ene 
• 432-16-6 1-trifluoro-methylnonafluorocyclohex-1-ene 

Relevant academic research and scientific papers

POLYFLUORO-COMPOUNDS BASED ON THE CYCLOHEPTANE RING SYSTEM. PART 1. COMPOUNDS DERIVED FROM TRIDECAFLUOROCYCLOHEPTANE

Partial fluorination of cycloheptane by cobaltic fluoride gave a mixture of polyfluorides, of which tridecafluorocycloheptane was present in significant proportions.With aqueous alkali this afforded dodecafluorocycloheptene, which with lithium aluminium hydride gave 1H-undecafluorocyclohept-1-ene.Each of these cyclo-olefins was oxidised to decafluoropimelic acid.Methanol/KOH reacted with dodecafluorocycloheptene to give mainly 1-methoxy-undecafluorocyclohept-1-ene together with ca 15percent of the 3-methoxy-isomer, and some 1,2-dimethoxydecafluorocyclohept-1-ene.The 1-methoxy-1-ene and cobaltic fluoride gave 1-methoxy- and 1-fluoromethoxytridecafluorocycloheptanone: the former was demethylated by sulphuric acid to dodecafluorocycloheptanone.The dichloro-adduct of the perfluoro-olefin was reduced by lithium aluminium hydride to a complex mixture, from which 1H/2H- and 1H,2H-dodecafluorocycloheptane were isolated.

FLUOROCYCLOHEXANES. PART XVI. THE SIX H-TRIFLUOROMETHYLDECAFLUORO- AND TWO OF THE 2H,4H-TRIFLUOROMETHYLNONAFLUORO-CYCLOHEXANES

Fluorination of benzotrifluoride by cobaltic fluoride at 260-280 deg gave, besides the fluorocarbon, the six possible tridecafluoromethylcyclohexane isomers, and two 2H,4H-dodecafluorides.Of the C7HF13 compounds, only the cis-2H-, and the cis- and trans-4H-isomers could be isolated pure.The two 3H-isomers were made by pyrolysis of perfluoro(1-methyl-3-isopropylcyclohexane) in the presence of toluene.The trans-2H-isomer was made by further fluorination of one of the 2H,4H-dodecafluorides.Aqueous potash and the cis-2H-tridecafluoride gave 1-trifluoromethylnonafluorocyclohex-1-ene, which with stronger alkali hydrolysed to 1-carboxynonafluorocyclohex-1-ene.The cis- and trans- 2H and 4H-tridecafluorides were dehydrofluorinated by sodium fluoride at 320-380 deg (the cis-isomer of each pair reacted faster than the trans-: axial versus equatorial hydrogen) to give, respectively, the 1-trifluoromethylnonafluoro-ene and the 4-trifluoromethyl-isomer.The latter was isomerised to the former by sodium fluoride at 500-600 deg.The 1-CF3-ene gave hexafluoroglutaric acid on oxidation with alkaline potassium permanganate.