75017-20-8

Basic information

• Product Name: 1,1,3-trimethylcyclobutane
• Synonyms: 1,1,3-trimethylcyclobutane
• CAS NO: 75017-20-8
• Molecular Weight: 98.1882
• Mol File: 75017-20-8.mol

Chemical Properties

• CAS DataBase Reference: 1,1,3-trimethylcyclobutane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1,3-trimethylcyclobutane(75017-20-8)
• EPA Substance Registry System: 1,1,3-trimethylcyclobutane(75017-20-8)

Safety Data

• Hazardous Substances Data: 75017-20-8(Hazardous Substances Data)

Upstream product

• 76207-22-2 1,2-dimethyl-3-(bromomethyl)cyclobutane 
• 75017-23-1 3-chloromethyl-1,1-dimethylcyclobutane 
• 76207-20-0 5-bromo-4,4-dimethylpent-1-ene 

Relevant articles and documents

gem-Dimethyl Effect in a Grignard Reagent Cyclization-Cleavage Rearrengament

(2,2-Dimethyl-4-penten-1-yl)magnesium bromide (1) is in equilibrium with its cyclic isomer, magnesium bromide (2).The equilibrium constant for this cyclization has a value of 2E-3.The gem-dimethyl substitution leads to an increase of a factor of about 22 in the equilibrium constant and also retards the rate of cleavage of 2.The sources of the gem-dimethyl effect in this system are discussed.

The Kinetics and Mechanism of Ring Opening of Radicals containing the Cyclobutylcarbinyl System

The kinetic parameters of β-fission of radicals containing the cyclobutylcarbinyl system have been determined by analysis of the mixtures obtained when suitable chloro-compounds are treated with tributylstannane.Under these conditions ring opening is irreversible and in the rigid bicyclic system (4) is under stereoelectronic control.For ring opening of cyclobutylcarbinyl radical (8) kf = 4.3 x 103 s-1 at 60 deg C, and the best values of the activation parameters appear to be ΔH(excit.) = 12.2 kcal mol-1 and ΔS(excit.) = -7.4 cal mol-1 K-1.Monocyclic systems undergo preferential fission of the more substituted βγ-bond.Methyl substituents at the α-, β-, or δ-positions have little effect but γ-substitution strongly enhances the rate of ring opening.The transition state is reactant-like and has a similar disposition of centres to that (1) for homolytic addition.