84846-06-0

Upstream product

• 81651-67-4 (3S,4S)-1,1-Dibromo-4-phenyl-spiro[2.2]pentane 
• 56152-84-2 1,1-dibromo-2-phenylspiro[2.2]pentane 
• 97173-22-3 <1-Benzyl-cyclopropyl-methyl>-trimethyl-ammonium - Iodid 
• 770738-66-4 1-bromo-4-phenylspiropentane 
• 75-11-6 diiodomethane 
• 2327-99-3 1-phenylpropadiene 
• 186581-53-3 diazomethane 
• 100-42-5 styrene 
• 252921-91-8 5-phenylspiro(1-pyrazoline-3,1'-cyclopropane) 
• 107432-65-5 1,1-dibromo-5-phenylspiro[2,2]pentane 

Downstream Products

• 13384-54-8 (Z)-(2-methylbut-1-en-1-yl)benzene 
• 3968-89-6 1-[(2-ethyl)-2-propenyl]benzene 

Relevant academic research and scientific papers

Aluminum carbenoids in allene cyclopropanation

The reactions of aluminum carbenoids with alkyl- and phenyl-substituted allenes and cyclic allenes are studied. An efficient method for the synthesis of substituted spiropentanes was developed. 1,2-Cyclononadiene was selectively converted into bicyclo[7.1.0]dec-1-ene. An unusual transformation of α-methylphenylallene into a spiroindane derivative under the action of Et3Al-CH2I2 was found.

Polylithiumorganic compounds. Part 29: C,C Bond cleavage of phenyl substituted and strained carbocycles using lithium metal

The reaction of phenyl substituted cyclopropanes phenylcyclopropane and 1,1-diphenylcyclopropane, phenyl substituted bicyclobutanes 1- phenylbicyclobutane, 1-methyl-3-phenylbicyclobutane, 1-methyl-2,2- diphenylbicyclobutane, as well as phenyl substituted spiropentanes phenylspiropentane and 1,1-diphenylspiropentane with lithium metal or lithium di-t-butylbiphenyl (LiDBB) was investigated. Under suitable reaction conditions and choice of solvent in all cases cleavage of the single bond next to the activating phenyl group was observed. The dilithiumorganic compounds thus obtained are sufficiently stable and can be trapped with electrophiles. Lithium hydride elimination is observed as follow-up reaction only in a few cases. The corresponding anions of the strained ring systems 1-lithio-2,2- diphenylcyclopropane, 1-lithio-3-phenylbicyclobutane, 1-lithio-3-methyl-2,2- diphenylbicyclobutane, and 1-lithio-4-phenylspiropentane, which can be obtained by lithium bromine exchange or by metalation of the unsubstituted carbocycle, do not show any cleavage upon reaction with lithium metal. The reaction of phenyl substituted cyclopropanes, bicyclobutanes as well as spiropentanes with lithium metal with formation of highly reactive dilithiumorganic compounds was investigated. In all cases cleavage of the bond next to the phenyl substituent(s) was observed.

Formation and thermal decomposition of adducts of phthalimidonitrene with spiro(1-pyrazolinecyclopropanes)

Oxidation of N-aminophthalimide with lead tetraacetate in the presence of spiro(1-pyrazolinecyclopropanes) at temperature from -20 °C to -30 °C resulted in the formal generation of phthalimidonitrene followed by its addition at the N=N bond of the pyrazoline ring to form 5(3)-substituted N-{spiro[1-pyrazolinio-3(5),1′-cyclopropane]}-N-phthalimidoamides (azimines), whose regioisomeric compositions were determined to a large extent by the nature of the substitueras in the pyrazoline ring. The structures of phthalimidoazimines were established based on the NMR spectra and X-ray diffraction data. Thermal conversions of the resulting adducts, which proceeded either with retention or with opening of the spiro-fused cyclopropane ring, were studied.

SPIROPENTANES. IV. TOTAL REDUCTION OF gem-DIBROMOSPIROPENTANES

The reductive debromination of gem-dihalogenospiropentanes with zinc in protic solvents and with lithium aluminum hydride in ether takes place readily and leads with good yields to hydrocarbons of the spiropentane series.The formation of deuterospiropenta