6165-88-4

Upstream product

• 7350-77-8 7-isopropylidene-benzo-bicyclo(2.2.1)heptene 
• 92885-23-9 benzonorborn-7-one azine 
• 29370-70-5 7,7-Dimethoxybenzonorbornen 
• 1072-85-1 o-fluorobromobenzene 
• 2175-91-9 6,6'-dimethyl fulvene 
• 7350-72-3 7-isopropylidenebenzonorbornadiene 
• 24472-15-9 1,2,3,4-Tetrachlor-1,4-dihydro-1,4-dimethoxymethanonaphthalin 
• 34201-94-0 1,4-dichloro-7,7-dimethoxybenzonorbornene 
• 1198-20-5 anti-benzonorbornen-9-ol 
• 92885-23-9 benzonorbornone azine 

Downstream Products

• 55255-94-2 anti-7-benzonorbornenol 
• 1198-20-5 anti-benzonorbornen-9-ol 
• 13999-10-5 1,2,3,4-tetrahydro-1,4-methanonaphthalene-9-anti-ol 
• 64725-57-1 syn-7-Methoxybenzonorbornen 
• 64725-57-1 anti-7-methoxybenzonorbornene 
• 14098-20-5 anti-9-aminobenzonorbornene 
• 34201-93-9 7-p-Tolyloxymethylenbenzonorbornen 

Relevant academic research and scientific papers

Bridged aromatic alkenes for the study of carbocation-π interaction

Toward the goal of gaining further insight into carbocation-π interactions, bridged-ring aromatic alkene model systems are being investigated in which one isomer will permit π complexation of an intramolecular tertiary carbocation with a benzene ring, but

SINGLET OXYGEN AND TRIAZOLINEDIONE ADDITION TO AZINES

Photooxygenation of azines, i.e., adamantanone azine (1) and benzonorborn-7-one azine (4), afforded in addition to the corresponding ketones, lactones derived from a carbonyl oxide intermediate via an electron transfer pathway.On the other hand, 4-substitued-1,2,4-triazoline-3,5-diones (TAD) react with azine 1 to give a 1,3-dipole, an azomethinimine intermediate as nitrogen analogue of a carbonyl oxide, which afforded the -cycloadducts in treatment with dipolarophiles.The mechanistic implications are discussed.

REACTION OF SINGLET OXYGEN WITH AZINES: IMPLICATIONS FOR DIOXIRANE INTERMEDIATE

Photooxygenation of tricyclodecanone azine (adamantanone azine) afforded, in addition to adamantanone, 4-oxohomoadamantan-5-one derived from a dioxirane intermediate via a non-radical pathway.

Electronic Control of Stereoselectivity. 8. The Stereochemical Course of Electrophilic Additions to Aryl-Substituted 9-Isopropylidenebenzonorbornenes

A series of aryl-substituted 9-isopropylidenebenzonorbornenes (1-4) and the parent 7-isopropylidenenorbornene (5) have been synthesized, and the stereochemistry of addition of numerous electrophiles to their exocyclic double bond has been determined.For assistance in interpreting the results, photoelectron spectroscopic investigations and extensive ZDO and MNDO/3 calculations were also undertaken.When weak electophiles reagents such as singlet oxygen, m-chloroperbenzoic acid, N-bromosuccinimide, N-methyltriazolinedione, and tert-butyl hypochlorite were studied, all gave product distributions which greatly favored anti addition when the aryl ring was unsubstituted or substituted by a pair of methoxyl groups.The placement of chlorine or fluorine groups on the aromatic ring was accompanied by a substantial enhancement in the relative amount of syn product.For strong electrophiles such as protonated tert-butyl hypochlorite, dichlorocarbene, the acetylinium cation, and protonated formaldehyde, syn attack was greatly favored or dominated exclusively.These marked crossovers in syn/anti stereoselection, which serve as a convenient tool with which to assess relative electrophilicity, may be explained in terms of the involvment of bridged or open ion pathways.Where bridged ions develop (weak electrophiles), long-range homoaromatic charge delocalization to the aromatic ring develops, with the result that anti attack becomes kinetically dominant.When powerfully electrophilic species are involved, this phenomenon is not important and transient aryl complex formation appears controlling.