Clay and acid catalysed isomerisation and cyclisation reactions of highly branched isoprenoid (HBI) alkenes: Implications for sedimentary reactions and distributions

Simon T. Belt, W. Guy Allard, Janne Rintatalo, Lesley A. Johns, Adri Van Duin, Steven J. Rowland

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

Several highly branched isoprenoid alkenes isolated from the diatom Haslea ostrearia have been subjected to laboratory simulations of early diagenetic reactions under mild acid conditions including addition of K-10 Montmorillonite clay. The products of these reactions have been found to be highly dependent on the degree of unsaturation of the alkenes. For dienes, double bond migration and geometric isomerisation are observed as the only reactions. In contrast, trienes undergo both isomerisation and rapid cyclisation reactions to yield substituted cyclohexenes. Molecular mechanics calculations have been performed to complement the laboratory experiments and to assist in proposing reaction mechanisms. The significance of these findings for the interpretation of the numerous reports of highly branched isoprenoids in Recent and ancient sediments is discussed. Copyright (C) 2000 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)3337-3345
Number of pages9
JournalGeochimica et Cosmochimica Acta
Volume64
Issue number19
DOIs
StatePublished - Nov 8 2000

Fingerprint

isoprenoid
alkene
Cyclization
Terpenes
Alkenes
Isomerization
Cyclohexenes
clay
Molecular mechanics
Acids
acid
montmorillonite
mechanics
Sediments
diatom
sediment
simulation
Experiments
distribution
montmorillonite K-10

All Science Journal Classification (ASJC) codes

  • Geochemistry and Petrology

Cite this

@article{2b5a295026694406b5e9a9dff57045f4,
title = "Clay and acid catalysed isomerisation and cyclisation reactions of highly branched isoprenoid (HBI) alkenes: Implications for sedimentary reactions and distributions",
abstract = "Several highly branched isoprenoid alkenes isolated from the diatom Haslea ostrearia have been subjected to laboratory simulations of early diagenetic reactions under mild acid conditions including addition of K-10 Montmorillonite clay. The products of these reactions have been found to be highly dependent on the degree of unsaturation of the alkenes. For dienes, double bond migration and geometric isomerisation are observed as the only reactions. In contrast, trienes undergo both isomerisation and rapid cyclisation reactions to yield substituted cyclohexenes. Molecular mechanics calculations have been performed to complement the laboratory experiments and to assist in proposing reaction mechanisms. The significance of these findings for the interpretation of the numerous reports of highly branched isoprenoids in Recent and ancient sediments is discussed. Copyright (C) 2000 Elsevier Science Ltd.",
author = "Belt, {Simon T.} and Allard, {W. Guy} and Janne Rintatalo and Johns, {Lesley A.} and {Van Duin}, Adri and Rowland, {Steven J.}",
year = "2000",
month = "11",
day = "8",
doi = "10.1016/S0016-7037(00)00444-0",
language = "English (US)",
volume = "64",
pages = "3337--3345",
journal = "Geochmica et Cosmochimica Acta",
issn = "0016-7037",
publisher = "Elsevier Limited",
number = "19",

}

Clay and acid catalysed isomerisation and cyclisation reactions of highly branched isoprenoid (HBI) alkenes : Implications for sedimentary reactions and distributions. / Belt, Simon T.; Allard, W. Guy; Rintatalo, Janne; Johns, Lesley A.; Van Duin, Adri; Rowland, Steven J.

In: Geochimica et Cosmochimica Acta, Vol. 64, No. 19, 08.11.2000, p. 3337-3345.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Clay and acid catalysed isomerisation and cyclisation reactions of highly branched isoprenoid (HBI) alkenes

T2 - Implications for sedimentary reactions and distributions

AU - Belt, Simon T.

AU - Allard, W. Guy

AU - Rintatalo, Janne

AU - Johns, Lesley A.

AU - Van Duin, Adri

AU - Rowland, Steven J.

PY - 2000/11/8

Y1 - 2000/11/8

N2 - Several highly branched isoprenoid alkenes isolated from the diatom Haslea ostrearia have been subjected to laboratory simulations of early diagenetic reactions under mild acid conditions including addition of K-10 Montmorillonite clay. The products of these reactions have been found to be highly dependent on the degree of unsaturation of the alkenes. For dienes, double bond migration and geometric isomerisation are observed as the only reactions. In contrast, trienes undergo both isomerisation and rapid cyclisation reactions to yield substituted cyclohexenes. Molecular mechanics calculations have been performed to complement the laboratory experiments and to assist in proposing reaction mechanisms. The significance of these findings for the interpretation of the numerous reports of highly branched isoprenoids in Recent and ancient sediments is discussed. Copyright (C) 2000 Elsevier Science Ltd.

AB - Several highly branched isoprenoid alkenes isolated from the diatom Haslea ostrearia have been subjected to laboratory simulations of early diagenetic reactions under mild acid conditions including addition of K-10 Montmorillonite clay. The products of these reactions have been found to be highly dependent on the degree of unsaturation of the alkenes. For dienes, double bond migration and geometric isomerisation are observed as the only reactions. In contrast, trienes undergo both isomerisation and rapid cyclisation reactions to yield substituted cyclohexenes. Molecular mechanics calculations have been performed to complement the laboratory experiments and to assist in proposing reaction mechanisms. The significance of these findings for the interpretation of the numerous reports of highly branched isoprenoids in Recent and ancient sediments is discussed. Copyright (C) 2000 Elsevier Science Ltd.

UR - http://www.scopus.com/inward/record.url?scp=0033785773&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0033785773&partnerID=8YFLogxK

U2 - 10.1016/S0016-7037(00)00444-0

DO - 10.1016/S0016-7037(00)00444-0

M3 - Article

AN - SCOPUS:0033785773

VL - 64

SP - 3337

EP - 3345

JO - Geochmica et Cosmochimica Acta

JF - Geochmica et Cosmochimica Acta

SN - 0016-7037

IS - 19

ER -