Reactions of 3а,6a-diaza-1,4-diphosphapentalene with activated acetylenes

The reaction of cyclohexane-annulated 3 a,6a-diaza-1,4-diphosphapentalene (DDP) with di- tert -butyl acetylenedicarboxylate (DBAD) affords the 1,3-dipolar cycloaddition product of the acetylene moiety to the phosphorus and sp 2 -carbon atoms of DDP in 90% yield. No individual products were isolated...

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Bibliographic Details
Published in:Russian chemical bulletin 2018-11, Vol.67 (11), p.2073-2078
Main Authors: Kornev, A. N., Galperin, V. E., Panova, Yu. S., Sushev, V. V., Cherkasov, A. V., Arapova, A. V., Abakumov, G. A.
Format: Article
Language:English
Subjects:
ACETYLENE
ATOMS
CARBAZOLES
CARBON
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Cycloaddition
CYCLOHEXANE
Full Articles
Inorganic Chemistry
INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY
Organic Chemistry
ORGANIC PHOSPHORUS COMPOUNDS
PHOSPHORUS
Reaction products
X-RAY DIFFRACTION
YIELDS
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Summary:The reaction of cyclohexane-annulated 3 a,6a-diaza-1,4-diphosphapentalene (DDP) with di- tert -butyl acetylenedicarboxylate (DBAD) affords the 1,3-dipolar cycloaddition product of the acetylene moiety to the phosphorus and sp 2 -carbon atoms of DDP in 90% yield. No individual products were isolated in the reaction of DDP with dimethyl acetylenedicarboxylate (DMAD). In the three-component DDP–DMAD–carbazole system (1: 2: 1), a product was generated in 73% yield via successive reactions, including the 1(P),3(C)-dipolar cycloaddition of DMAD to DDP, the addition of the second equivalent of DMAD to the three-coordinate phosphorus atom of the intermediate, and the NH addition of carbazole at the unsaturated C=C bond of the second DMAD moiety. The structures of the reaction products were established by X-ray diffraction.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-018-2331-0