The Cycloaddition Reactions of Some 7-Alkylidenecycloocta-1,3,5-trienes

1990 ◽  
Vol 43 (3) ◽  
pp. 463 ◽  
Author(s):  
PH Ferber ◽  
GE Gream ◽  
PK Kirkbride ◽  
ERT Tiekink
Keyword(s):  
Maleic Anhydride ◽  
Cycloaddition Reactions ◽  
Dimethyl Acetylenedicarboxylate ◽  
Chlorosulfonyl Isocyanate ◽  
Diethyl Azodicarboxylate

A number of 7-alkylidenecycloocta-1,3,5-trienes, all unstable, yield novel π8+π2 cycloadducts with a range of π2-addends. The reactions of 7-methylenecycloocta-1,3,5-triene with ethene-tetracarbonitrile, 4- phenyl-1,2,4-triazoline-3,5-dione, diethyl azodicarboxylate and chlorosulfonyl isocyanate are described. The tetraene did not react with maleic anhydride or dimethyl acetylenedicarboxylate. As well, the reactions of 1,3,5-trimethyl-7-methylenecycloocta-1,3,5-triene, 2,9a- dihydro-1H-cyclopentacyclooctene and 1,2,3,10a- tetrahydrobenzocyclooctene with ethenetetracarbonitrile and of 7- isopropylidenecycloocta-1,3,5-triene with 4-phenyl-1,2,4-triazoline- 3,5-dione are discussed. The intermediacy of homotropylium zwitterions in the reactions is postulated.

Cycloheptatriene Norcaradiene Equilibrium in Dimethyl trans-3,8-Dihydroheptalene-3,8-dicarboxylate

1993 ◽  
Vol 46 (10) ◽  
pp. 1613 ◽  
Author(s):  
A Menzek ◽  
M Balci
Keyword(s):  
Maleic Anhydride ◽  
Singlet Oxygen ◽  
Dimethyl Fumarate ◽  
Diels Alder ◽  
Dimethyl Acetylenedicarboxylate ◽  
Catalysed Reaction ◽  
Diethyl Azodicarboxylate

Diels-Alder cycloadditions of dienophiles , such as 4-phenyl-1,2,4-triazoline-3,5-dione, dimethyl acetylenedicarboxylate, dimethyl fumarate , diethyl azodicarboxylate , maleic anhydride, benzyne and p-benzoquinone, to dimethyl trans-3,8-dihydrohexalene-3,8-dicarboxylate (4) have been investigated, and monoaddition products (9)-(16) have been isolated. It has been shown that a second addition to this system occurs only with singlet oxygen and with benzyne. Furthermore, it has been established that the second addition is retarded because of the strain in the cycloheptatriene molecule. The anti bicyclic endoperoxides (21)-(25) formed have been converted, either on heating or in a Co( tpp )- catalysed reaction, into the corresponding bisepoxides (27)-(31).

Cycloaddition reactions of indenes. 2. Reactions with dimethyl acetylenedicarboxylate and maleic anhydride

1980 ◽  
Vol 45 (23) ◽  
pp. 4564-4572 ◽  
Author(s):  
Wayland E. Noland ◽  
Venkataraman Kameswaran ◽  
Lawrence L. Landucci
Keyword(s):  
Maleic Anhydride ◽  
Cycloaddition Reactions ◽  
Dimethyl Acetylenedicarboxylate

1,3-Dipolar Cycloaddition Reactions of the Ylide Derived from 6-Phenacyl-benzo[f][1,7]naphthyridinium Bromide

1999 ◽  
Vol 52 (2) ◽  
pp. 149 ◽  
Author(s):  
Grazyna Matusiak
Keyword(s):  
Maleic Anhydride ◽  
Methyl Methacrylate ◽  
Methacrylic Acid ◽  
Basic Medium ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Dimethyl Acetylenedicarboxylate ◽  
Methyl Vinyl ◽  
Acid Methyl

The 1,3-dipolar cycloaddition reactions of 4,6-diazaphenanthrene 6-phenacylide formed in situ from the quaternary 6-phenacylbenzo[f][1,7]naphthyridinium bromide in basic medium were examined; methacrylic acid, methyl methacrylate, butyl vinyl ether, methyl vinyl ketone, maleic anhydride and dimethyl acetylenedicarboxylate were used as the dipolarophiles.

Cycloaddition Reactions of the Methano[10]annulene Derivative 9,9-Dichloro-1,4-dihydro-4a,8a-methanonaphthalene

1991 ◽  
Vol 44 (4) ◽  
pp. 555 ◽  
Author(s):  
B Halton ◽  
SGG Russell
Keyword(s):  
Maleic Anhydride ◽  
Lewis Acid ◽  
Acid Catalysis ◽  
Cycloaddition Reactions ◽  
Dimethyl Acetylenedicarboxylate ◽  
Lewis Acid Catalysis ◽  
Inverse Electron Demand ◽  
Hydrophilic Solvent ◽  
Electron Demand

9,9-Dichloro-1,4-dihydro-4a,8a-methanonaphthalene (4) adds the electron-deficient dienophiles 4-phenyl-1,2,4-triazoline-3,5-dione, maleic anhydride and dimethyl acetylenedicarboxylate to the α-face to give adducts (5)-(7) respectively; the addition of the alkyne requires Lewis acid catalysis. Inverse electron-demand addition of 3,6-diphenyl-1,2,4,5-tetrazine to the monoene component of (4) in hydrophilic solvent (ethane-1,2-diol) is thwarted; the CCl2 bridge is ejected and the 1,4-dihydronaphthalene formed is captured to give (ultimately) phthalazine (16). Dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate adds to (4) to give the methanobenzophthalazine (17b).

Cycloaddition reactions. Addition of dimethyl acetylenedicarboxylate to 1-dimethylaminoindene

1970 ◽  
Vol 48 (11) ◽  
pp. 1633-1638 ◽  
Author(s):  
Terrence W. Doyle
Keyword(s):  
Ring Opening ◽  
Cycloaddition Reactions ◽  
Dimethyl Acetylenedicarboxylate ◽  
Reaction Conditions

The cycloaddition of 1-dimethylaminoindene (2) to dimethyl acetylenedicarboxylate to form a fused cyclobutene system 3 is discussed. Compound 3 underwent two modes of ring opening to yield either the indene–maleate system 4 or the benzocycloheptatriene system 5 depending on reaction conditions. The synthesis of a number of multifunctional benzotropones from 5 is discussed.

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