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

E. Alexander Hill; Daniel C. Link; Peter Donndelinger

doi:10.1021/jo00319a026

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

E. Alexander Hill, Daniel C. Link, Peter Donndelinger

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Abstract

(2,2-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.

Original language	English
Pages (from-to)	1177-1182
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	46
Issue number	6
DOIs	https://doi.org/10.1021/jo00319a026
State	Published - Mar 1981

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title = "gem-Dimethyl Effect in a Grignard Reagent Cyclization-Cleavage Rearrangement",

abstract = "(2,2-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.",

author = "{Alexander Hill}, E. and Link, {Daniel C.} and Peter Donndelinger",

year = "1981",

month = mar,

doi = "10.1021/jo00319a026",

language = "English",

volume = "46",

pages = "1177--1182",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

number = "6",

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T1 - gem-Dimethyl Effect in a Grignard Reagent Cyclization-Cleavage Rearrangement

AU - Alexander Hill, E.

AU - Link, Daniel C.

AU - Donndelinger, Peter

PY - 1981/3

Y1 - 1981/3

N2 - (2,2-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.

AB - (2,2-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.

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U2 - 10.1021/jo00319a026

DO - 10.1021/jo00319a026

M3 - Article

AN - SCOPUS:0011239231

SN - 0022-3263

VL - 46

SP - 1177

EP - 1182

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 6

ER -

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

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