Acetylenedicarboxylate dimethyl ester

Dimethyl acetylenedicarboxylate gave first a similar adduct (2) which then added further molecules of furan yielding (3) and subsequently (4). Between 1931 and 1940 the reactions of acetylenedi-carboxylic acid and its dimethyl ester with a number of nitrogen containing heterocyclic compounds were examined, and structures were proposed for the products. Apart from an unpublished investigation of the products from pyridine and dimethyl acetylenedicar-... 

Diels et al. showed that acetylenedicarboxylic acid and 1-methyl-pyrrole gave l-methyl-2-pyrrylmaleic anhydride (41) and a second compound. The anhydride on hydrogenation and conversion to the corresponding dimethyl ester gave the same product as obtained from 1-methylpyrrole and maleic anhydride, followed by hydrolysis and... 

Methylindole and acetylenedicarboxylic acid is reported to give two unidentified products, but with the dimethyl ester the crs and trans (61) adducts were obtained. It was suggested that the major product had the trans configuration but this was not proved. Hydrogenation of both adducts gave the corresponding succinic ester, which was also obtained from 2-methylindole and maleic anhydride, followed by esterification. 

In numerous synthetic studies,9" 6 100 it has been demonstrated that porphyrins react at the chromophore periphery in cycloaddition reactions, rearrangements, conjugative additions and substitution reactions to yield interesting porphyrin derivatives. Thus, metal-free protoporphyrin IX dimethyl ester reacts in Diels-Alder reactions108a b with dienophilcs like ethenetetra-carbonitrile and acetylenedicarboxylates at the diene structural parts to yield, according to the reaction conditions, the corresponding monoadducts 2 and 3 (see also Section 1.2.) and bisadducts 1 (see also Section 1.4.), respectively. 

Diethyl azodicarboxylate is usually abbreviated to DEAD. However, the same abbreviation is used for diethyl acetylenedicarboxylate. To avoid confusion, it is proposed that DEAZD should be used to abbreviate the azo ester. Similarly, DMAZD will be used for the dimethyl ester. Recently, the abbreviation DAZD has also been suggested B, M. Jacobson, D. Gerhard, C. Jackson, and J. Smallwood, J. Org. Chem. 45, 3344 (1980). 

Acetylenedicarboxylic acid, dimethyl ester, 50, 25, 36 Acetylenes, reaction with tri-methylsilyl azide, 50, 109 Acetylenic sulfonium salts, furans from, 53, 3 2-Acetylindane-l,3-dione, 52, 4 2-ACETYL-6-METHOXYNAPHTHALENE, 53, 5... 

Contrarily, diethyl acetylenedicarboxylate (276b) with quinaldine gives far fewer isolable products than does the dimethyl ester it affords no quinolizine but instead actually gives pyridoazepine 284 and cyclobu-taindolizine 281b. 

Dimethyl acetylenedicarboxyl ate Acetylenedicarboxylic acid, dimethyl ester (8) 2-Butynedioic acid, dimethyl ester (9) (762-42-5)... 

DIMETHYL ACETYLENEDICARBOXYLATE (Acetylenedicarboxylic acid, dimethyl ester)... 

Having sufficient amounts of these novel dienes in hand opens the field for further study. Cycloaddition of acetylenedicarboxylic acid dimethyl ester (ADDE) to [3]dendralene 7 in toluene first afforded the l l-adduct 43, which by a second addition of ADDE provided the expected 2 l-adduct 44. After this had been aromatized by treatment with DDQ to the naphthalene derivative 45, a double benzannulation could be carried out as described in Scheme 8 [13]. 

It was demonstrated some time ago that vinylic and cross-conjugated double bonds of protoporphyrin (IX) dimethyl ester (80a) constitute a diene system capable of undergoing Diels-Alder reactions with activated dieno-philes (68CC697). Isobacteriochlorins 81 and 82a were obtained in a reaction with dimethyl acetylenedicarboxylate (ACDE) and tetracyanoethene (TCNE), respectively (73JCS(PI)1424). 

Propargyl bromide 1-Propyne, 3-bromo- (8,9) (106-96-7) Dimethyl acetylenedicarboxylate Acetylenedicarboxylic acid, dimethyl ester (8) 2-Butynedioic acid, dimethyl ester (9) (762-42-5) l,2-Hexadien-5-yne (8,9) (33142-15-3)... 

The hydrogenation of acetylenedicarboxylic acid dimethyl ester (80) and diphenylacetylene (83) with [RhH2(0C(==0)0H)(PPr 3)2] gives dimethyl fumarate (82) and fraws-stilbene (84), respectively. This complex also catalyzes an isomerization of ds-stilbene to fra s-stilbene, though hydrogenation of alkyne is about eight times faster than the isomerization. ... 

Acetylenedicarboxylic acid, dimethyl ESTER, 32, SS Acetylenic glycols, 39, 57 2- -Acetylphenylhydroquinone, 84,1 S-ACETYL-n-VALERIC ACID, 31, 3 Acid chlorides, 39, 19 synthesis of, 37, 69... 

Addition of dimethyl acetylenedicarboxylate to give pyrazole-3,4,S-tricarboxylic acid dimethyl ester monoazide ... 

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