Regiochemical Control in Triptycene Formation—An Exercise in Subtle Balancing Multiple Factors

Jan Hendrik Lamm; Yury V. Vishnevskiy; Eric Ziemann; Beate Neumann; Hans Georg Stammler; Norbert W. Mitzel

doi:10.1002/open.201700196

Regiochemical Control in Triptycene Formation—An Exercise in Subtle Balancing Multiple Factors

Jan Hendrik Lamm, Yury V. Vishnevskiy, Eric Ziemann, Beate Neumann, Hans Georg Stammler, Norbert W. Mitzel

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

8 Scopus citations

Abstract

Reactions between 1,8-dichloroanthracenes with substituents in position 10 and ortho-chloroaryne afford mixtures of 1,8,13- (syn) and 1,8,16-trichlorotriptycenes (anti). The syn/anti ratio is dependent on these substituents. Electropositive substituents like SiMe₃ and GeMe₃ lead to preferred formation of the syn-isomer, whereas CMe₃ groups exclusively afford the anti-isomer. Different quantum chemical calculations including location of transition states give conflicting results, but indicate the importance of dispersion forces for an at least qualitative prediction of results. The syn-trichlorotriptycenes with SiMe₃ and GeMe₃ substituents were characterized by using NMR spectroscopy, mass spectrometry, and X-ray diffraction experiments.

Original language	English
Pages (from-to)	111-114
Number of pages	4
Journal	ChemistryOpen
Volume	7
Issue number	1
DOIs	https://doi.org/10.1002/open.201700196
State	Published - 1 Jan 2018
Externally published	Yes

Keywords

anthracenes
cycloaddition
dispersion
solid-state structures
triptycenes

ASJC Scopus subject areas

General Chemistry

Access to Document

10.1002/open.201700196

Cite this

@article{1ba81737a0e0462fafaa80edb589021f,

title = "Regiochemical Control in Triptycene Formation—An Exercise in Subtle Balancing Multiple Factors",

abstract = "Reactions between 1,8-dichloroanthracenes with substituents in position 10 and ortho-chloroaryne afford mixtures of 1,8,13- (syn) and 1,8,16-trichlorotriptycenes (anti). The syn/anti ratio is dependent on these substituents. Electropositive substituents like SiMe3 and GeMe3 lead to preferred formation of the syn-isomer, whereas CMe3 groups exclusively afford the anti-isomer. Different quantum chemical calculations including location of transition states give conflicting results, but indicate the importance of dispersion forces for an at least qualitative prediction of results. The syn-trichlorotriptycenes with SiMe3 and GeMe3 substituents were characterized by using NMR spectroscopy, mass spectrometry, and X-ray diffraction experiments.",

keywords = "anthracenes, cycloaddition, dispersion, solid-state structures, triptycenes",

author = "Lamm, {Jan Hendrik} and Vishnevskiy, {Yury V.} and Eric Ziemann and Beate Neumann and Stammler, {Hans Georg} and Mitzel, {Norbert W.}",

note = "Publisher Copyright: {\textcopyright} 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.",

year = "2018",

month = jan,

day = "1",

doi = "10.1002/open.201700196",

language = "English",

volume = "7",

pages = "111--114",

journal = "ChemistryOpen",

issn = "2191-1363",

publisher = "John Wiley & Sons Inc.",

number = "1",

}

TY - JOUR

T1 - Regiochemical Control in Triptycene Formation—An Exercise in Subtle Balancing Multiple Factors

AU - Lamm, Jan Hendrik

AU - Vishnevskiy, Yury V.

AU - Ziemann, Eric

AU - Neumann, Beate

AU - Stammler, Hans Georg

AU - Mitzel, Norbert W.

PY - 2018/1/1

Y1 - 2018/1/1

N2 - Reactions between 1,8-dichloroanthracenes with substituents in position 10 and ortho-chloroaryne afford mixtures of 1,8,13- (syn) and 1,8,16-trichlorotriptycenes (anti). The syn/anti ratio is dependent on these substituents. Electropositive substituents like SiMe3 and GeMe3 lead to preferred formation of the syn-isomer, whereas CMe3 groups exclusively afford the anti-isomer. Different quantum chemical calculations including location of transition states give conflicting results, but indicate the importance of dispersion forces for an at least qualitative prediction of results. The syn-trichlorotriptycenes with SiMe3 and GeMe3 substituents were characterized by using NMR spectroscopy, mass spectrometry, and X-ray diffraction experiments.

AB - Reactions between 1,8-dichloroanthracenes with substituents in position 10 and ortho-chloroaryne afford mixtures of 1,8,13- (syn) and 1,8,16-trichlorotriptycenes (anti). The syn/anti ratio is dependent on these substituents. Electropositive substituents like SiMe3 and GeMe3 lead to preferred formation of the syn-isomer, whereas CMe3 groups exclusively afford the anti-isomer. Different quantum chemical calculations including location of transition states give conflicting results, but indicate the importance of dispersion forces for an at least qualitative prediction of results. The syn-trichlorotriptycenes with SiMe3 and GeMe3 substituents were characterized by using NMR spectroscopy, mass spectrometry, and X-ray diffraction experiments.

KW - anthracenes

KW - cycloaddition

KW - dispersion

KW - solid-state structures

KW - triptycenes

UR - http://www.scopus.com/inward/record.url?scp=85041573476&partnerID=8YFLogxK

U2 - 10.1002/open.201700196

DO - 10.1002/open.201700196

M3 - Article

AN - SCOPUS:85041573476

SN - 2191-1363

VL - 7

SP - 111

EP - 114

JO - ChemistryOpen

JF - ChemistryOpen

IS - 1

ER -

Regiochemical Control in Triptycene Formation—An Exercise in Subtle Balancing Multiple Factors

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this