4663-22-3

Usage

InChI:InChI=1/C6H10/c1-5(2)6-3-4-6/h6H,1,3-4H2,2H3

Upstream product

• 930-39-2 2-cyclopropyl-2-propanol 
• 17396-98-4 2,2'-dicyclopropyl-2,2'-azopropane 
• 108-98-5 thiophenol 
• 7664-93-9 sulfuric acid 
• 108-88-3 toluene 
• 67-56-1 methanol 
• 104131-89-7 <1-(1-Methylethyl)cyclopropyl>nitrosocarbamidsaeure-methylester 

Downstream Products

• 1003-17-4 2,2-dimethyltetrahydrofuran 
• 765-43-5 Cyclopropyl methyl ketone 
• 107-83-5 2-Methylpentane 
• 25522-55-8 3-phenyl-2-cyclopropyl-1-propene 
• 911796-43-5 2-phenyl-2-(1-methoxy-2-cyclopropylprop-2-yl)pyrrolidine 
• 139537-52-3 2-chloro-3-methyl-3-cyclopropylcyclobutanone 
• 119489-90-6 Z-1-iodo-5-para toluene sulphonyl pent-3-en 
• 119489-89-3 E-1-iodo-5-para toluene sulphonyl pent-3-en 
• 117734-74-4 1-Methyl-4-((E)-2-methyl-5-phenylselanyl-pent-2-ene-1-sulfonyl)-benzene 
• 117734-73-3 1-Methyl-4-((E)-2-methyl-5-phenylselanyl-pent-2-ene-1-sulfonyl)-benzene 
• 625-27-4 2-methyl-2-pentene 
• 3638-35-5 2-cyclopropylpropane 
• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 184356-00-1 ((E)-5-Chloro-2-methyl-pent-2-enylsulfanyl)-benzene 

Relevant academic research and scientific papers

Clocking Tertiary Cyclopropylcarbinyl Radical Rearrangements

Three independent methods have been employed to estimate the rate constant, k1, for ring-opening of the 2-cyclopropyl-2-propyl radical, 1, at room temperature. These three estimates are based on chemical trapping of 1 and the ring-opened 4-methylpent-3-ene-1-yl radical by thiophenol (k1 = (1.65 ± 0.41) × 107 M-1 s-1), 9-azabicyclo[3.3.1]nonane-N-oxyl (k1 = (1.76 ± 0.34) × 107 M-1 s-1) and 2,2,6,6-tetramethylpiperidine-N-oxyl (k1 = (2.1 ± 0.4) × 107 M-1 s-1) and absolute rate constants for nonrearranging radicals structurally related to 1. The mean value for k1) ((1.84 ± 0.4) × 107 M-1 s-1) should be used when 1 is employed as a tertiary alkyl free radical clock at ambient temperatures.

Photolysis of β-Azo Perester, a Bifunctional Initiator. The Fragmentation Rate of a β-Peroxy Ester Radical Determined by the Cyclopropylcarbinyl Clock Method

Two free radical initiators containing an azo group and a perester moiety on adjacent carbons have been prepared.On long wavelength UV irradiation, these compounds lose nitrogen to afford β-perester radicals.The cyclopropylcarbinyl radical clock technique has been used to determine that the lifetime of these radicals at 25 deg C toward β-scission and decarboxylation is 480 ns.The potential utility of β-azo peresters as bifunctional free radical initiators is briefly discussed.

Deamination Reactions, 44. Decomposition of 1-Alkylcyclopropanediazonium Ions

1-Methyl- (17), 1,2-dimethyl- (41, 44), 1-propyl- (64), 1-(1-methylethyl)cyclopropanediazonium ions (80), and -1-diazonium ions (93) have been generated by alkaline cleavage of the analogous nitrosocarbamates in methanol.Cyclopropyl-allyl transformation and nucleophilic displacement were the only reactions of 17, 41, 44, and 93 while elimination and 1,2-shifts of an α-hydrogen compete increasingly with 64 and 80.The stereochemistry of ring cleavage and nucleophilic displacement has been explored, using 2-D labels in the case of 17 and 93.Cyclopropanediazonium ions (1) and 41 react stereospecifically, 17 and 44 are moderately stereoselective (ca. 85:15), and 93 is entirely unselective.The data indicate a gradual changeover from concerted to stepwise mechanisms.Appreciable stabilization of the positive charge is required to reach the SN1 extreme.