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

Journal Article · Thu Nov 15 04:00:00 EST 2018 · Russian Chemical Bulletin

DOI:https://doi.org/10.1007/S11172-018-2331-0· OSTI ID:22943396

Galperin, V. E.; Panova, Yu. S.; Sushev, V. V.; Cherkasov, A. V.; Arapova, A. V.; Abakumov, G. A. ^[1]

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1. Russian Academy of Sciences, G. A. Razuvaev Institute of Organometallic Chemistry (Russian Federation)

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{sup 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.

• OSTI ID: 22943396
• Journal Information: Russian Chemical Bulletin, Journal Name: Russian Chemical Bulletin Journal Issue: 11 Vol. 67; ISSN RCBUEY; ISSN 1066-5285
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
ACETYLENE
ATOMS
CARBAZOLES
CARBON
CYCLOHEXANE
ORGANIC PHOSPHORUS COMPOUNDS
PHOSPHORUS
X-RAY DIFFRACTION
YIELDS