Thermal isomerization of trimethyl cyclopentadienes

J.W. Haan, de; H. Kloosterziel

doi:10.1002/recl.19680870309

Thermal isomerization of trimethyl cyclopentadienes

J.W. Haan, de, H. Kloosterziel

Chemical Engineering and Chemistry

Research output: Contribution to journal › Article › Academic › peer-review

41 Citations (Scopus)

Abstract

The thermal behavior of 1,5,5 and 2,5,5-trimethylcyclopentadiene has been investigated. The following isomerizations have been observed and their activation parameters detd.: 1,5,5-TMCPD -> 1,2,3-TMCPD, DH.++. = 40.3 kcal./mole, DS.++. = -1 cal./degree mole; 2,5,5-TMCPD -> 1,2,4-TMCPD, DH.++. = 44.2 kcal./mole, DS.++. = +6 cal./degree mole; and 2,5, 5-TMPCD -> 1,2,3-TMCPD, DH.++. = 44.4 kcal./mole, DS.++. = +3 cal./degree mole. Evidence is presented that these reactions occur by an intramol., sigmatropic 1,5 shift of a Me group. 20 references. [on SciFinder (R)]

Original language	English
Pages (from-to)	298-307
Journal	Recueil des Travaux Chimiques des Pays-Bas
Volume	87
Issue number	3
DOIs	https://doi.org/10.1002/recl.19680870309
Publication status	Published - 1968

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title = "Thermal isomerization of trimethyl cyclopentadienes",

abstract = "The thermal behavior of 1,5,5 and 2,5,5-trimethylcyclopentadiene has been investigated. The following isomerizations have been observed and their activation parameters detd.: 1,5,5-TMCPD -> 1,2,3-TMCPD, DH.++. = 40.3 kcal./mole, DS.++. = -1 cal./degree mole; 2,5,5-TMCPD -> 1,2,4-TMCPD, DH.++. = 44.2 kcal./mole, DS.++. = +6 cal./degree mole; and 2,5, 5-TMPCD -> 1,2,3-TMCPD, DH.++. = 44.4 kcal./mole, DS.++. = +3 cal./degree mole. Evidence is presented that these reactions occur by an intramol., sigmatropic 1,5 shift of a Me group. 20 references. [on SciFinder (R)]",

author = "{Haan, de}, J.W. and H. Kloosterziel",

year = "1968",

doi = "10.1002/recl.19680870309",

language = "English",

volume = "87",

pages = "298--307",

journal = "Recueil des Travaux Chimiques des Pays-Bas",

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publisher = "Royal Netherlands Chemical Society",

number = "3",

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TY - JOUR

T1 - Thermal isomerization of trimethyl cyclopentadienes

AU - Haan, de, J.W.

AU - Kloosterziel, H.

PY - 1968

Y1 - 1968

N2 - The thermal behavior of 1,5,5 and 2,5,5-trimethylcyclopentadiene has been investigated. The following isomerizations have been observed and their activation parameters detd.: 1,5,5-TMCPD -> 1,2,3-TMCPD, DH.++. = 40.3 kcal./mole, DS.++. = -1 cal./degree mole; 2,5,5-TMCPD -> 1,2,4-TMCPD, DH.++. = 44.2 kcal./mole, DS.++. = +6 cal./degree mole; and 2,5, 5-TMPCD -> 1,2,3-TMCPD, DH.++. = 44.4 kcal./mole, DS.++. = +3 cal./degree mole. Evidence is presented that these reactions occur by an intramol., sigmatropic 1,5 shift of a Me group. 20 references. [on SciFinder (R)]

AB - The thermal behavior of 1,5,5 and 2,5,5-trimethylcyclopentadiene has been investigated. The following isomerizations have been observed and their activation parameters detd.: 1,5,5-TMCPD -> 1,2,3-TMCPD, DH.++. = 40.3 kcal./mole, DS.++. = -1 cal./degree mole; 2,5,5-TMCPD -> 1,2,4-TMCPD, DH.++. = 44.2 kcal./mole, DS.++. = +6 cal./degree mole; and 2,5, 5-TMPCD -> 1,2,3-TMCPD, DH.++. = 44.4 kcal./mole, DS.++. = +3 cal./degree mole. Evidence is presented that these reactions occur by an intramol., sigmatropic 1,5 shift of a Me group. 20 references. [on SciFinder (R)]

U2 - 10.1002/recl.19680870309

DO - 10.1002/recl.19680870309

M3 - Article

SN - 0165-0513

VL - 87

SP - 298

EP - 307

JO - Recueil des Travaux Chimiques des Pays-Bas

JF - Recueil des Travaux Chimiques des Pays-Bas

IS - 3

ER -

Thermal isomerization of trimethyl cyclopentadienes

Abstract

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