Deca-2,8-diene

Flash vacuum pyrolysis of tricyclo[7.1.0.04,6]deca-2,7-diene 544 is accompanied by a long cascade of rearrangements leading to various azulenes (equation 214)266. The structures of these products were determined by using the chlorine atoms as labels for the 13C NMR measurements. 

An interesting 1,2-divinylcyclopropane isomerization is observed when 5,5,10,10-tetrachlorotricyclo[7.1.0.09,6]deca-2,7-diene is subjected to flash vacuum pyrolysis at 700 °C and 10-4Torr a mixture of three isomeric dichloroazulenes is produced [215]. 

Cyclooctatetraene/diazo ester 1 1.2 tetramethyl an/i-tricyclo[7.1.0.0 ]deca-2,4-diene-7,7,10,10-tetraearboxylate (7%) was also formed together with tetramethyl jyn-tricyclo[7.1.0.0 - ]deca-2,7-diene-5,5,10,10-tetracarboxylate (2%). 

Cyclopropan--[Pg.3520]

E,E-Deca-2,7-diene CH3CHCHCH2(CH2)3CHCHCH3 81.6 341.6 Correlation 2005DEN/TUM... 

Treatment of 5,5,10,10-tetrabromotricyclo[7.1.0.0" ]deca-2,7-diene with methyl-lithium at -78°C gave naphthalene (Scheme 11.9). ... 

Trifluoroacetate, trifluoroacetic acid, MeOH Butadiene 1,1,1,10,10,10-Hexafluoro-3,7 -deca-diene, other products 257)... 

The next approach for obtaining higher molecular weight polymers was to explore acyclic diene metathesis (ADMET) polymerizations.The aim was to achieve higher molecular weight flame-resistant polymers. We modeled the reaction using aliphatic diene monomers such as 1,5-hexadiene and 1,9-deca-diene under test conditions to optimize conditions before making BPC-derived products. At this point, we decided to functionalize the BPC with an olefin. 

A similar rearrangement was used in a stereoselective synthesis of (if, )-3,7-dimethyT2,6-deca-diene-l,10-diol (pheromone of the queen butterfly) in six steps from gcraniol (Table 3, entry 16)310. Use of 2-methoxy-l,3-butadienes and related compounds (e.g., unsaturated acetals311) allows an iterative Claisen rearrangement by reduction of the resulting enone28,309. 

This reaction is a convenient method for the synthesis of polyenes. Generally the acychc olefin used is ethylene, which by interaction with cyclopentene, cyclooctene or cyclohexene gives 1,6-heptadiene, 1,9-deca-diene and 1,7-octadiene, respectively. Most studies in this field have involved heterogeneous systems like Mo(CO)6—AI2O3 or CoO—M0O3— Al2O3 [10]. 

An ipso attack on the fluorine carbon position of 4-fIuorophenol at -40 °C affords 4-fluoro-4-nitrocyclohexa-2 5-dienone in addtion to 2-nitrophenol The cyclodienone slowly isomenzes to the 2-nitrophenol Although ipso nitration on 4-fluorophenyl acetate furnishes the same cyclodienone the major by-product is 4 fluoro-2,6-dinitrophenol [25] Under similar conditions, 4-fluoroanisole pnmar ily yields the 2-nitro isomer and 6% of the cyclodienone The isolated 2 nitro isomer IS postulated to form by attack of the nitromum ion ipso to the fluorine with concomitant capture of the incipient carbocation by acetic acid Loss of the elements of methyl acetate follows The nitrodienone, being the keto tautomer of the nitrophenol, aromatizes to the isolated product [26] (equation 20) Intramolecular capture of the intermediate carbocation occurs in nitration of 2-(4-fluorophenoxy)-2-methyIpropanoic acid at low temperature to give the spiro products 3 3-di-methyl-8 fluoro 8 nitro-1,4 dioxaspiro[4 5]deca 6,9 dien 2 one and the 10-nitro isomer [2d] (equation 21)... 

The reaction of oxepin with dimethyl 5-oxo-2,3-diphenylcyclopenta-l,3-diene-l,4-dicarboxy-late takes a different course. Two products 7 and 8 can be isolated, 7 is the [4 + 2] adduct of the cyclopentadienone across the central C-C double bond of the oxepin, the other, 8, is thought to be a [4+6] cycloadduct across the triene system of the oxepin.237 In boiling benzene, the [4 + 2] adduct 7 undergoes no cycloreversion, but rearranges to the tricyclo[5.3.02,4]deca-5,8-dien-10-one system.237 The [4+6] adduct, however, is stable under thermal conditions. 

CYCLOBUTADIENE IN SYNTHESIS endo-TRICYCLO[4.4.0.02 5]DECA-3,8-DIEN-7,IO-DIONE... 

The synthesis of fUido-tricyclo[4.4.0.02 5]deca-3,8-dien-7,10-dione and verification of its endo-configuration has been reported earlier.3 This adduet is a useful starting material for the syntheses of tetracyclo-[5.3.0.02 6.03 10]deca-4,8-diene,s tricyclo[4.4.0.02 5]deca-3,7,9-triene,6 cis, syn, cjs-tricyclo[5.3.0.02,6]deca-4,8-dien-3,10-dione,7 and 4-oxahexa-cyclo[5.4.0.02 6.03 10.05 9.08,11]undecane.a... 

The recent upsurge of interest in systems of theoretical interest demands practical syntheses of several important compounds. These are BICYCLO[2.l.0]PENT-2-ENE, BENZOCYCLOPROPENE, 1,6-OXIDO[10]ANNULENE, and others. ewdo-TRICYCLO[4.4.0.02 5]-DECA-3,8-DIENE-7,10-DIONE is utilized as a model for the use of CYCLOBUTADIENE IN SYNTHESIS, and a stable monomeric ketene, icri-BUTYLCYANOKETENE offers opportunities for further studies of this interesting species. 

Various LC-PB-MS and LC-APCI-MS comparisons have been reported on polymer additive extracts [540, 563,629,630]. The complementary character of the El and APCI modes was confirmed. Yu et al. [630] compared LC-PB-MS and RPLC-UV-APCI-MS for detection and identification of unknown additives (in the 252 to 696 Da range) in an acetonitrile extract from PP (containing Irganox 1076, Naugard XL-1 and a degradation product, NC-4, 3-(3,5-di-f-butyl-4-hydroxyphenyl) propanoic acid, 7,9-di-f-butyl-l-oxaspiro [4,5] deca-6,9-diene-2,8-dione and octadecanol-1). Comparison was based on El data (identification of chemical structure), APCI (MW information CID spectrum with limited fragmentation) and PDA (210 nm). The components were identified by El and confirmed by APCI- (with better sensitivity and linearity) MS and PDA showed... 

Acetylene Compounds. XIV. The Occurrence of 2-trans-8-trans-Deca-2 8-diene-4 6-diyn-l-ol = trans trans-Matricarianol in Nature. Acta Chem. Scand. 8, 34 (1954). 

Pristomyrmex pungens W-PG Trail following antennal response Deca-2,4-dien-5-olide 141 [185]... 

The naming of these three heterocyclic fused (5 5 5) ring systems has been carried out according to the IUPAC system of nomenclature. Some examples are given as follows compound la (Table 1) is named (3-hydroxy-4-methoxyphenylthieno[2,3-3]pyrrolizin-8-one. Compound 15a (Table 2) is dithieno[3,2-3 2, 3 - 1thiophene. Compound 23a (Table 2) is dithieno[3,2-3 2, 3 - 1pyrrole. Compound 20a (Table 2) is dithicno[3,2-3 2, 3 -r/]thiophene-4,4-dio ide. Compound 13b (Table 2) is 3,4-dimethyldithieno[3,2-3 2, 3 -i/]thiophene-7,7-dioxide. Compound 38 (Table 4) is fM, r, r-10-azatricyclo[5.2.1.01 10]deca-2,5,8-triene. Compound 39 (Table 4) is cis,cis, m-10-azatricyclo[5.2.1.01 10]deca-2,8-diene. The nomenclature of compound 40 (Table 4) is 1,4,7 triaza tricy-clo[5.2.1.01,10]decane. 

Tetrazine (171) and its derivatives are electron-deficient cycloaddends, which undergo [4 + 2] cycloadditions with inverse electron demand. When bicyclopropylidene (3) was added to a dichloromethane solution of 171, its red color disappeared within 1.5 h at room temperature. The white crystalline product isolated in 86% yield turned out to be a mixture of at least two stereoisomeric compounds 174, trimers of the 8,9-diazadispiro[2.0.2.4]deca-7,9-diene (173) evidently formed via the normal [4 + 2]-cycloadduct 172 after nitrogen extrusion (Scheme 25) [13b]. 

A variety of other highly-strained electron-rich donors also form colored complexes (similar to homobenzvalene) with various electron acceptors, which readily undergo thermal cycloadditions (with concomitant bleaching of the color).209 For example, Tsuji et al.210 reported that dispiro[2.2.2.2]deca-4,9-diene (DDD), with an unusually low ionization potential of 7.5 eV,211 readily forms a colored charge-transfer complex with tetracyanoquinodimethane (TCNQ). The [DDD, TCNQ] charge-transfer complex undergoes a thermal cycloaddition to [3,3]paracyclophane in excellent yield, i.e.,... 

The l,7-dioxaspiro[4,5]deca-3,9-diene 11 can be prepared by both a double RCM and by sequential single RCMs (Scheme 5) . 

Dimethyl tricyclo[4.2.2.02 -5]deca-3,7-diene-9,10-dicarboxylate adds bromine and iodine only to the less hindered double bond to give the syn 1,2-addition product of the cyclobutene moiety79. The product composition from this compound depends on the temperature and the solvent. At high temperatures, the 1,2-addition predominates over the transannular reaction, but this predominance is small in a solvent like chloroform and is lost in a protic solvent such as acetic acid (equation 47). 

Electrophilic addition of IN3 to the tricyclo[4.2.2.02,5]deca-3,7-diene derivative 60 has been reported92,93 to give exclusively or predominantly the syn azido iodide 61... 

The stereochemistry and the mechanism of the electrophilic additions to tricyclo[4.2. 2.02,5]deca-3,7-diene derivatives have been studied frequently, although some unambiguous... 

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