Dimethyl-4-penten-l-yl)magnesium bromide (1) is in equilibrium with its cyclic isomer, [(3,3-dimethylcyclobutyl)methyl]magnesium bromide (2). The equilibrium constant for this cyclization has a value of 2 X 10~3. 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.Because of the strain inherent in the small ring, ringcleavage rearrangements of the cyclobutylmethyl1 (k'0 in eq 1) and cyclopropylmethyl2 Grignard reagents proceed essentially to completion.3 Although the equilibrium
Das N,N‐Dichlor‐methyl‐cyclohexylamin (I) ergibt bei der Behandlung mit Kupfer(I)‐ Chlorid in Dimethylsulfoxid unter Stickstoff bei Raumtemperatur die Desaminierungsprodukte (II) und (III).
Das Gleichgewicht zwischen den beiden Grignardverbindungen (I) und (II) wird untersucht und der Einfluß der geminalen Dimethy1‐Substitution auf die Lage des Gleichgewichtes diskutiert.
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