82988-74-7

Downstream Products

• 121829-58-1 (1R,4R,5S,6S,7R)-6,7-Dichloro-4-(2-chloro-phenyl)-2,3-diaza-bicyclo[3.2.0]hept-2-ene 
• 99557-39-8 4-(2-Chloro-phenyl)-3-hydroxy-1H-quinolin-2-one 
• 121829-24-1 (1S,4S,5R,6R,7S)-7-Chloro-4-(2-chloro-phenyl)-6-methylsulfanyl-2,3-diaza-bicyclo[3.2.0]hept-2-ene 
• 121829-40-1 (1S,4S,5R,6R,7S)-4-(2-Chloro-phenyl)-6,7-bis-methylsulfanyl-2,3-diaza-bicyclo[3.2.0]hept-2-ene 
• 89-98-5 2-chloro-benzaldehyde 
• 118-91-2 ortho-chlorobenzoic acid 
• 107135-21-7 1-chlorocyclohepta-1,2,4,6-tetraene 
• 15684-93-2 C₇H₅ClNO 
• 25144-38-1 (E)-2,2'-dichlorostilbene 
• 20657-43-6 (Z)-1,2-bis(2-chlorophenyl)ethene 
• 5328-80-3 N,N'-Bis-[1-(2-chloro-phenyl)-meth-(E)-ylidene]-hydrazine 

Relevant academic research and scientific papers

1,2,4,6-CYCLOHEPTATETRAENE: THE KEY INTERMEDIATE IN ARYLCARBENE INTERCONVERSIONS AND RELATED C7H6 REARRANGEMENTS

Thermolysis or photolysis of phenyldiazomethane (2) produces phenylmethylene (3), which ring-expands to give 1,2,4,6-cycloheptatetraene (6).Spectroscopic and chemical evidence rule out bicyclo(4.1.0)hepta-2,4,6-triene (4), cycloheptatrienylidene (5), and bicyclo(3.2.0)hepta-1,3,6-triene (11) intermediates.The strained allene in cycloheptatetraene (6) exhibits infrared absorption at 1824 and 1816 cm-1.Deuterium substitution produces the expected 10-cm-1 shift in the allene absorption.Fluorine or chlorine substitution substantially enhances the allene absorption intensity.Deuterium labeling studies reveal that the intramolecular chemistry of cycloheptatetraene (6) involves reversible thermal or photochemical equilibriation with phenylmethylene (3).The intermolecular chemistry of 6 involves dimerization.At temperatures as low as 10 K, 6 forms a labile (2+2) dimer,7, which undergoes thermally allowed, electrocyclic ring opening to give heptafulvalene (8) upon warming to room temperature.The rearrangements of 7-acetoxynorbornadiene (9), 2-diazobicyclo(3.2.0)hepta-3,6-diene (31), and 8-diazobicyclo(2.2.2)octa-2,5-dien-7-one (33) all involve cycloheptatetraene (6) intermediates.

Chemiluminescence from arylcarbene oxidation: phenylchlorocarbene and (2-chlorophenyl)carbene

Chemiluminescence is observed in the thermal reaction of phenylchlorocarbene or (2-chloro-phenyl)carbene and O2, matrix-isolated in Ar.The chemiluminescence spectra closely match the phosphorescence of the corresponding carbonyl compounds.The reactivity of both carbenes towards O2 is very different.Singlet carbene phenylchlorocarbene reacts thermally only slowly with O2 up to 60 K.The oxidation products phenylchloroformate, benzoyl chloride and O(3P) are mainly formed photochemically on irradiation of the diazirine precursor.Triplet carbene (2-chlorophenyl)carbene reacts readily with O2 at cryogenic temperatures to give mostly 2-chlorobenzaldehyde-O-oxide.The carbonyl-O-oxide is photochemically easily cleaved to give 2-chlorobenzaldehyde and O(3P).The reaction step leading to carbonyl compounds in their excited states is in both carbene oxidations the recombination of the free carbene and O(3P).