An in depth study of the formation of new tetrathiafulvalene derivatives from 1,8-diketones

Figen Turksoy; John D. Wallis; Umit Tunca; Turan Ozturk

doi:10.1016/j.tet.2003.08.042

An in depth study of the formation of new tetrathiafulvalene derivatives from 1,8-diketones

Figen Turksoy, John D. Wallis, Umit Tunca, Turan Ozturk^*

^*Corresponding author for this work

Department of Chemistry

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

38 Citations (Scopus)

Abstract

A detailed study of the reactions of phosphorus pentasulfide and Lawesson's reagent with a series of 4,5-bis(RCOCH ₂S)-1,3-dithiole-2-thiones (R=Ph, 4-MeOC₆H₄, 4-Br C₆H₄, Me) has been carried out. These reactions lead to fusion of either an unsaturated 1,4-dithiin ring or a thiophene to the dithiole; the former in higher yield, while the latter is a significant product in the reactions with Lawesson's reagent; as well as small amounts of minor products. A mechanistic rationalization of these products is discussed in some detail. The new fused dithioles have been converted to novel series of fused TTF derivatives.

Original language	English
Pages (from-to)	8107-8116
Number of pages	10
Journal	Tetrahedron
Volume	59
Issue number	41
DOIs	https://doi.org/10.1016/j.tet.2003.08.042
Publication status	Published - 6 Oct 2003

Keywords

1,4-dithiin
1,8-diketone ring formation
BEDT-TTF
TTF
Thiophene

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10.1016/j.tet.2003.08.042

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title = "An in depth study of the formation of new tetrathiafulvalene derivatives from 1,8-diketones",

abstract = "A detailed study of the reactions of phosphorus pentasulfide and Lawesson's reagent with a series of 4,5-bis(RCOCH 2S)-1,3-dithiole-2-thiones (R=Ph, 4-MeOC6H4, 4-Br C6H4, Me) has been carried out. These reactions lead to fusion of either an unsaturated 1,4-dithiin ring or a thiophene to the dithiole; the former in higher yield, while the latter is a significant product in the reactions with Lawesson's reagent; as well as small amounts of minor products. A mechanistic rationalization of these products is discussed in some detail. The new fused dithioles have been converted to novel series of fused TTF derivatives.",

keywords = "1,4-dithiin, 1,8-diketone ring formation, BEDT-TTF, TTF, Thiophene",

author = "Figen Turksoy and Wallis, \{John D.\} and Umit Tunca and Turan Ozturk",

year = "2003",

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doi = "10.1016/j.tet.2003.08.042",

language = "English",

volume = "59",

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journal = "Tetrahedron",

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T1 - An in depth study of the formation of new tetrathiafulvalene derivatives from 1,8-diketones

AU - Turksoy, Figen

AU - Wallis, John D.

AU - Tunca, Umit

AU - Ozturk, Turan

PY - 2003/10/6

Y1 - 2003/10/6

N2 - A detailed study of the reactions of phosphorus pentasulfide and Lawesson's reagent with a series of 4,5-bis(RCOCH 2S)-1,3-dithiole-2-thiones (R=Ph, 4-MeOC6H4, 4-Br C6H4, Me) has been carried out. These reactions lead to fusion of either an unsaturated 1,4-dithiin ring or a thiophene to the dithiole; the former in higher yield, while the latter is a significant product in the reactions with Lawesson's reagent; as well as small amounts of minor products. A mechanistic rationalization of these products is discussed in some detail. The new fused dithioles have been converted to novel series of fused TTF derivatives.

AB - A detailed study of the reactions of phosphorus pentasulfide and Lawesson's reagent with a series of 4,5-bis(RCOCH 2S)-1,3-dithiole-2-thiones (R=Ph, 4-MeOC6H4, 4-Br C6H4, Me) has been carried out. These reactions lead to fusion of either an unsaturated 1,4-dithiin ring or a thiophene to the dithiole; the former in higher yield, while the latter is a significant product in the reactions with Lawesson's reagent; as well as small amounts of minor products. A mechanistic rationalization of these products is discussed in some detail. The new fused dithioles have been converted to novel series of fused TTF derivatives.

KW - 1,4-dithiin

KW - 1,8-diketone ring formation

KW - BEDT-TTF

KW - TTF

KW - Thiophene

UR - https://www.scopus.com/pages/publications/0141459268

U2 - 10.1016/j.tet.2003.08.042

DO - 10.1016/j.tet.2003.08.042

M3 - Article

AN - SCOPUS:0141459268

SN - 0040-4020

VL - 59

SP - 8107

EP - 8116

JO - Tetrahedron

JF - Tetrahedron

IS - 41

ER -

An in depth study of the formation of new tetrathiafulvalene derivatives from 1,8-diketones

Abstract

Keywords

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