1714-38-1

Upstream product

• 67-56-1 methanol 
• 544-25-2 Cyclohepta-1,3,5-triene 
• 26811-28-9 tropylium cation 
• 32315-05-2 bis-(p-N,N-dimethylaminophenyl)phenylmethyl methyl ether 

Downstream Products

• 539-80-0 Tropone 
• 29304-86-7 7-(4-chlorophenyl)-cyclohepta-1,3,5-triene 
• 73968-33-9 7-<β,β-Bis-(p-dimethylamino-phenyl)-vinyl>-tropiliden 
• 93308-05-5 7-<3-Chlor-phenyl>-tropiliden 
• 63543-77-1 4-Cycloheptatrienyliden-2,6-dimethyl-cyclohexadienon 
• 93867-72-2 7-(3-Methoxy-phenyl)-tropiliden 
• 1643-95-4 7-(m-fluorophenyl)tropylidene 
• 71096-17-8 7-(3-Methylphenyl)-cyclohepta-1.3.5-trien 
• 29304-88-9 7-(4-Tolyl)-1,3,5-cycloheptatrien 
• 93307-90-5 7-<3-Brom-phenyl>-tropiliden 
• 54615-31-5 1-bromo-4-(cyclohepta-2,4,6-trien-1-yl)benzene 
• 92191-50-9 7-(4-Methylmercapto-phenyl)-tropiliden 
• 94026-68-3 7-(3-Dimethylamino-phenyl)-tropiliden 
• 1541-11-3 7-phenylcycloheptatriene 

Relevant academic research and scientific papers

ANODIC TRANSFORMATION OF CYCLOHEPTATRIENE TO TROPONE AND TROPOLONE

Cycloheptatriene (CHT) has been directly transformed to 7-methoxycycloheptatriene (7-MCHT), an equivalent compound to a tropolium salt, by the anodic oxidation of CHT in methanol.The further anodic oxidation of 3-MCHT prepared from 7-MCHT has been found to be an effective method of synthesis of tropone and tropolone.

The Relative Electrophilic Reactivities of Tropylium Cation and its (OC)3M ?-Complexes: Kinetic Studies of Alkoxide Transfer and Reversible Nucleophilic Addition

?-Complexation of the tropylium cation (Tr)(1+) with an (OC)3Cr group increases thermodynamic stability (ΔpKR+ ca. 4.3 in methanol) and reduces reactivity towards abstraction of methoxide ion from Malachite Green methyl ether (MG)OMe (krel. ca. 110) in MeNO2 - MeCOEt (40:60 v/v) and nucleophilic exoaddition of methanol (krel. ca. 2100) in methanol.The organometallic cation (1a) is stable in aqueous solutions of pH(1+), (1+), and (1+) in MeNO2-MeCOEt (40:60 v/v) are 1:10:6, respectively.The rates of transfer to (Tr)(1+) of alkoxide ion from (η-7-exo-alkoxycycloheptatriene)Cr(CO)3 complexes (2a-d) in MeCN decrease through the series: alkoxy=methoxy>ethoxy>isopropoxy>t-butoxy, but the overall rate change is only about five-fold.In methanol, the 7-exo-methoxycycloheptatriene complex (2a) is about ten times more reactive towards acid heterolysis than is methyl tropyl ether.This conversion is general acid-catalysed.In aqueous solutions of pH>ca. 6, the rate of spontaneous heterolysis of the ether (2a) is substantially faster than that of consumption of the resulting cation (1a) which increases with increasing pH.The 7-endo-methoxy stereoisomer (3) is inert to acid heterolysis in aqueous solutions to give cation (1a), but undergoes decomplexation to give (Tr)(1+).

CYCLOHEPTATRIENYL-PHOSPHORUS DERIVATIVES. AN ABNORMAL PHOSPHONIUM SALT HYDROLYSIS.

A variety of cycloheptatrienyl-phosphorus derivatives have been prepared.In no case was evidence obtained of contribution from norcaradiene forms.Attempts to prepare the corresponding ylide from cycloheptatrienyltriphenylphosphonium salts led to substitution of phospine, as did reactions with a variety of nucleophiles, including hydroxide ion where the observed reaction is in conflict with earlier reports.