286-85-1

Usage

InChI:InChI=1/C11H8/c1-2-4-9-6-11-7-10(11)5-8(9)3-1/h1-6H,7H2

Upstream product

• 119-61-9 benzophenone 
• 92012-56-1 1.1-bis-(trimethylsilyl)-1H-cyclopropa{b}naphthalene 
• 479-33-4 2,3,4,5-tetraphenylcyclopenta-2,4-dienone 
• 61440-88-8 bis(2,4,6-trimethylphenyl)cyclopropenone 

Downstream Products

• 243-17-4 2,3-benzofluorene 
• 1592-38-7 2-Naphthalenemethanol 
• 75067-09-3 2-Vinyliden-2H-inden 
• 122408-45-1 (naphthalen-2-ylmethyl)(phenyl)sulfane 
• 13579-08-3 6,13-dihydropentacene 
• 21969-45-9 1,2-bis(2-naphthyl)ethane 
• 135-48-8 pentacene 
• 112223-66-2 6,7-dihydropentaphene 
• 2506-41-4 1-chloromethylnaphthalene 
• 91-57-6 2-Methylnaphthalene 
• 38287-05-7 2-(cyclohexylmethyl)naphthalene 
• 435274-63-8 4-methoxy-N-(naphth-2-ylmethyl)benzenamine 

Relevant academic research and scientific papers

C6H4 valence bond isomers: A reactive bicyclopropenylidene

(Chemical Equation Presented) The simple bicyclopropenylidene derivative 21b, stabilized by fusion into naphthalene, results from reaction of dimesitylcyclopropenone 20b with the 1-trimethylsilyl-1H-cyclopropa[d] naphthalenyl anion. Although unstable in air, the molecule survives ambient conditions long enough for separation and mass spectral characterization. Aerial oxidation of 21 b leads to 2,3-dimesitylanthracene-1,4-dione 22b whose X-ray crystal structure has been determined. While diphenylcyclopropenone 20a does not give identifiable products, the di-tert-butyl analogue 20c gives quinone 22c but in lower yield.

Studies in the Cycloproparene Series: Unexpected Products from Peterson Olefinations

Reaction of tetraphenylcyclopentadienone with anion 8 derived by monodesilylation of 1,1-bis(trimethylsilyl)cyclopropa[b]naphthalene (10) gives the 1-(5′-cyclopentadienyl)-substituted cycloproparene 17 from simple anion addition to the carbonyl group rather than fulvalene 16 from loss of Me3SiO-. Reactions of anion 8 with p-(trifluoromethyl)benzaldehyde and thiophene-2-carbaldehyde give the expected exocyclic olefins 12a and 12b, respectively. In contrast, the 3,6-dimethoxy analogue 24, obtained from cycloproparene 20, gives the C1 unsubstituted cycloproparene 19 and the Tishchenko products, p-(trifluoromethyl)benzyl p-(trifluoromethyl)benzoate (21) and 2-thienylmethyl thiophene-2-carboxylate (22), respectively. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Studies in the cycloproparene series: 1 chemistry of the 1-trimethylsilyl-1H-cyclopropa[b]naphthalenyl anion

Desilylation of 1,1-bis(trimethylsilyl)-1H-cyclopropa[b]naphthalene 10 with tert-butoxide or hydroxide ion gives anion 9 as a highly reactive species. Formed with tert-butoxide 9 can be intercepted by iodomethane to give the 1-methyl-1-trimethylsilyl deri

Synthesis of Cycloproparenes via Aromatization of 7-Oxanorbornenes with Low-Valent Titanium

1H-Cyclopropanaphthalene 3c and the 2,7-diphenyl-substituted derivative 3a have been synthesized via cycloaddition of the appropriate isobenzofurans 1a and 1b to 1-bromo-2-chlorocyclopropene and aromatization of the adducts with low-valent Ti.The same procedure afforded the 2,7-dimethyl-1H-cyclopropaisoquinoline (15), but failed for the parent azacompound.Reaction of adducts of furans to 1-bromo-2-chlorocyclopropenes with low-valent Ti produced mixtures of cyclopropabenzenes 19 and 1,6-dihalogeno-1,3,5-cycloheptatrienes 18.The latter could be converted to cyclopropabenzenes with BuLi.