13303-30-5

Upstream product

• 563-79-1 2,3-Dimethyl-2-butene 
• 93633-18-2 1,1-dibromo-2,2-dichloro-3,3-dimethylcyclopropane 
• 99235-97-9 3-bromo-1,1-dichloro-2,2-dimethylcyclopropane 
• 99236-10-9 3,3-dimethyl-1,1,2,2-tetrabromocyclopropane 
• 6214-32-0 1-bromo-3-methylbuta-1,2-diene 
• 1111-97-3 3-chloro-3-methylbut-1-yne 

Downstream Products

• 1781-49-3 1,1-Dimethyl-2,3-bis-cyclopropan 
• 32113-16-9 1-(2'.2'.3'.3'-Tetramethylcyclopropyl)-2-methyl-1-oxo-2-propyl-m-chlorbenzoat 
• 58873-32-8 [2-Methyl-1-(2,2,3,3-tetramethyl-cyclopropyl)-propenylsulfanyl]-benzene 
• 1341205-97-7 5,5-dimethyl-2,3-diphenyl-4-tetramethylcyclopropylidene-isoxazolidine 
• 1341205-98-8 3-(4-chlorophenyl)-5,5-dimethyl-2-phenyl-4-tetramethylcyclopropylidene-isoxazolidine 

Relevant academic research and scientific papers

Arylation of alkenylidenecyclopropanes via Heck reaction. A simple access to arylallylidenecyclopropanes

Five alkenylidenecyclopropanes have been arylated using a catalytic amount of [Pd(C3H5)Cl]2 (0.004%) associated to the tetradentate ligand cis, cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane or Tedicyp as t

A flexible Route to 1-Bromo-2-alkylcyclopropenes

1,1,2-Tribromocyclopropanes undergo 1,2-debromination with a dialkyl phosphite and either a trialkylamine or sodium hydride to form the corresponding 1-bromocyclopropene.

The Preparation and Lithiation of 1-Halogenocyclopropenes

Reaction of a range of 1,1,2-trihalogenocyclopropanes (halogen = bromine, chlorine) with methyl-lithium in ether at -90 - 20 deg C leads to 1,2-dehalogenation to the corresponding 1-halogenocyclopropene.The halogenocyclopropenes are readily lithiated by lithium-halogen exchange with a second equivalent of methyl-lithium to give 1-lithiocyclopropenes, which are in turn trapped by electrophiles; an exception to this is compound (21; X = Cl), which leads to 3-methylbuta-1,2-dienylidene (31) by initial lithium-hydrogen exchange and loss of lithium chloride.The cyclopropenes (5; R = Me, X = Br or Cl) and (21; X = Br or Cl) decompose even at temperatures around ambient, leading either to enynes (6; R = Me) or halogenoalkynes (18; X = Br or Cl).A 12C-labelling study indicates that C-1 of the cyclopropene (21; X = Cl) becomes C-2 of the alkyne (18; X = Cl) on rearrangement.

LABELLING STUDIES OF THE RING OPENING OF 1-BROMO-2-CHLORO-3,3-DIMETHYLCYCLOPROPENE

1-Bromo-2-chloro-3,3-dimethylcyclopropene reacts with methyl lithium in the presence of 2,3-dimethylbut-2-ene at above -70 deg C to give (4); 12C labelling shows that C-2 of the cyclopropane becomes the centre carbon of the allene.