154657-02-0

Basic information

• Product Name: 2-allyl-2-methylmalononitrile
• Synonyms: 2-allyl-2-methylmalononitrile
• CAS NO: 154657-02-0
• Molecular Weight: 120.154
• Mol File: 154657-02-0.mol

Chemical Properties

• CAS DataBase Reference: 2-allyl-2-methylmalononitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-allyl-2-methylmalononitrile(154657-02-0)
• EPA Substance Registry System: 2-allyl-2-methylmalononitrile(154657-02-0)

Safety Data

• Hazardous Substances Data: 154657-02-0(Hazardous Substances Data)

Upstream product

• 24850-33-7 allyltributylstanane 
• 138976-63-3 methyliodomalononitrile 
• 3696-36-4 2-methylmalononitrile 
• 106-95-6 allyl bromide 

Downstream Products

• 1318776-55-4 R-(-)-benzyl 2-carbamyl-2-methylpent-4-enoate 
• 1318776-68-9 (R)-benzyl 2-carbamoyl-2-methyl-7-phenylhept-4-enoate 
• 1318776-69-0 (S)-2-amino-2-methyl-7-phenylheptanoic acid 
• 1318776-71-4 (R,E)-6-benzyl 1-ethyl 5-carbamoyl-5-methylhex-2-enedioate 
• 1318776-73-6 (R)-1-benzyl 6-ethyl 2-carbamoyl-2-methylhexanedioate 

Relevant articles and documents

Catalytic Anti-Markovnikov Transformations of Hindered Terminal Alkenes Enabled by Aldehyde-Selective Wacker-Type Oxidation

A new strategy for the functionalization of sterically hindered terminal olefins is reported. Alkenes bearing quaternary carbons at the allylic or homoallylic position are readily oxidized to the corresponding aldehydes by palladium/copper/nitrite catalysis. A broad range of functional groups including esters, nitriles, silyl ethers, vinylogous esters, ketones, lactones, and β-ketoesters are tolerated under the reaction conditions. The crude aldehyde products can be transformed further, enabling direct conversion of hindered terminal alkenes to various other synthetically useful functional groups, resulting in formal anti-Markovnikov hydroamination, among other transformations.

Palladium Catalysed Direct Allylation of Pronucleophiles with Allylstannanes

The reaction of pronucleophiles 1 with allyltributylstannanes in the presence of catalytic amounts of Pd2(dba)3*CHCl3 (4 molpercent) and 1,2-bis(diphenylphosphino)ethane (dppe) (10 molpercent) at room temperature gives the corresponding allylation products in good to high yields.

Radical reaction initiated and stereocontrolled by zinc chloride

The reaction of allyltributyltin with methyl 2-[N-((4S)-4-(1-methylethyl)-2-oxazolidinone-3-carbamoyl)amino]-2-bromoacetate (5 a) was accelerated at -50°C in the presence of AIBN and stopped in the presence of galvinoxyl, indicating that the reaction proceeds through a radical mechanism. The reaction was accelerated dramatically at -78°C in the presence of ZnCl2·OEt2, and the ZnCl2-mediated reaction was stopped in the presence of galvinoxyl. In the presence of 2 equiv ZnCl2·OEt2, the reaction afforded methyl (2R)-2-[N-((4SH-(1-methylethyl)-2-oxazolidinone-3-carbamoyl)amino]-4-pentenoate {6a(R)} with high diastereoselectivity (93:7). Taken together, ZnCl2·OEt2 works as a radical initiator as well as chelating agent.