TY - JOUR

T1 - New π‐Extended 1,1′‐Disubstituted Ferrocenes with Thioate and Dithioate End Groups

AU - Schmiel, Sinem Fatma

AU - Butenschön, Holger

N1 - Funding Information: We thank Ms. Christina Schrand, M. Sc., for assistance in the synthesis of compound 17, and Dr. Gerald Dräger, Institut für Organische Chemie, Leibniz Universität Hannover, and Dr. Andreas Schaate, Institut f?r Anorganische Chemie, Leibniz Universität Hannover, for performing the crystal structure analyses. Open access funding enabled and organized by Projekt DEAL.

PY - 2021/5/5

Y1 - 2021/5/5

N2 - Extended π systems based on 1,1′-aryl or (2-arylethynyl) disubstitution at ferrocene with thioate or dithioate end groups are reported. In the context of molecular electronics, such end groups are possible alternative end groups for the attachment of molecular wires at gold surfaces. The respective thioates were successfully prepared in high yields via the respective carboxylic acid derivatives. Subsequent treatment with Lawesson's reagent led to the respective dithioates. However, this did not work in the presence of triple bonds, in these cases, product mixtures were formed. On the basis of literature evidence with Woollin's reagent, the selenium analog of Lawesson's reagent, one product was tentatively characterized as a double cyclization product of two triple bonds and two molecules of Lawesson's reagent. Preliminary experiments towards the formation of gold complexes by reaction with a Johnphos gold(I) salt are included.

AB - Extended π systems based on 1,1′-aryl or (2-arylethynyl) disubstitution at ferrocene with thioate or dithioate end groups are reported. In the context of molecular electronics, such end groups are possible alternative end groups for the attachment of molecular wires at gold surfaces. The respective thioates were successfully prepared in high yields via the respective carboxylic acid derivatives. Subsequent treatment with Lawesson's reagent led to the respective dithioates. However, this did not work in the presence of triple bonds, in these cases, product mixtures were formed. On the basis of literature evidence with Woollin's reagent, the selenium analog of Lawesson's reagent, one product was tentatively characterized as a double cyclization product of two triple bonds and two molecules of Lawesson's reagent. Preliminary experiments towards the formation of gold complexes by reaction with a Johnphos gold(I) salt are included.

KW - Extended π-Systems

KW - Ferrocene

KW - Gold Complexes

KW - Synthetic methods

UR - http://www.scopus.com/inward/record.url?scp=85108293187&partnerID=8YFLogxK

U2 - 10.1002/ejoc.202100335

DO - 10.1002/ejoc.202100335

M3 - Article

VL - 2021

SP - 2388

EP - 2401

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 0365-5490

IS - 17

ER -