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

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.

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).

ChemInform Abstract: Cycloaddition Reactions of 2-Acetylamino-, 2-Alkylamino-, 8-Ethylamino- , and 8-Acetylamino-1-azaazulenes with Dimethyl Acetylenedicarboxylate.

ChemInform ◽  
2010 ◽  
Vol 23 (44) ◽  
pp. no-no
Author(s):  
N. ABE ◽  
Y. FUKAZAWA ◽  
Y. HIRAI ◽  
T. SAKURAI ◽  
K. URUSHIDO ◽  
...  
Keyword(s):  
Cycloaddition Reactions ◽  
Dimethyl Acetylenedicarboxylate

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.

Sign in / Sign up

Export Citation Format

Share Document