Subscribe to RSS
DOI: 10.1055/s-0028-1088112
Malonyl Dichloride
Publication History
Publication Date:
02 April 2009 (online)
![](https://www.thieme-connect.de/media/synlett/200907/lookinside/thumbnails/10.1055-s-0028-1088112-1.jpg)
Introduction
Malonyl dichloride, or malonyl chloride CH2(COCl)2, is widely used in organic synthesis as a versatile biselectrophilic reagent. This compound has been used mainly in acylation (O-, S-, N-, C-acylation) and alkylation reactions. It is a convenient reagent for the preparation of heterocyclic derivatives [¹-8] and is utilized as an important building block in the synthesis of supramolecular compounds [9-¹²] with several applications. An attractive use of malonyl dichloride is the formation of the bicyclo[3.3.1]nonane-trione system [¹³-¹5] in a one-pot reaction. Compounds containing this bicyclo system are common features incorporated into the structures of numerous natural products. Malonyl dichloride must be handled with precaution because it is lachrymating and corrosive. Due to the reaction with water it decomposes when exposed to wet air.
- 1
Lalaev BY.Yakovlev IP.Zakhs VE. Russ. J. Gen. Chem. 2006, 76: 133 - 2
Yavari I.Souri S. Synlett 2007, 2969 - 3
Karaböcek N.Karaböcek S.Mazlum H.Degirmencioglu I.Serbest K. Turk. J. Chem. 2004, 28: 87 - 4
Fürstner A.Feyen F.Prinz H.Waldmann H. Tetrahedron 2004, 60: 9543 - 5
Luo G. Tetrahedron Lett. 2004, 45: 8331 - 6
Diana P.Carbone A.Barraja P.Martorana A.Gia O.DallaVia L.Cirrincione G. Bioorg. Med. Chem. Lett. 2007, 17: 6134 - 7
Brondel N.Renoux B.Gesson JP. Tetrahedron Lett. 2006, 47: 9305 - 8
Jiang XP.Cheng Y.Shi GF.Kang ZM. J. Org. Chem. 2007, 72: 2212 - 9
dos Santos LJ.Alves RB.Freitas RP.Nierengarten JF.Magalhães LEF.Krambrock K.Pinheiro MVB. J. Photochem. Photobiol. A: Chem. 2008, 200: 277 - 10
Jung M.Tak J.Chung WY.Park KK. Bioorg. Med. Chem. Lett. 2006, 16: 1227 - 11
Iehl J.Freitas RP.Nicot BD.Nierengarten JF. Chem. Commun. 2008, 2450 - 12
Chronakis N.Hirsch A. C. R. Chimie 2006, 9: 862 - 13
Ahmad NM.Rodeschini V.Simpkins NS.Ward SE.Blake AJ. J. Org. Chem. 2007, 72: 4803 - 14
Rodeschini V.Ahmad NM.Simpkins NS. Org. Lett. 2006, 8: 5283 - 15
Nuhant P.David M.Pouplin T.Delpech B.Marazano C. Org. Lett. 2007, 9: 87 - 16
Vogel AI. Vogel’s Textbook of Practical Organic Chemistry 5th ed.: Pearson Education; England: 1989. p.692 - 17
McCloshey AL.Fonken GS.Kluiber RW.Johnson WS.Raha C. Org. Synth. 1954, 34: 26