Alkyl Substituted [2.2]Paracyclophane-­‐1,9-­‐dienes

Benjamin Lidster; Dharam Kumar; Andrew Spring; Chin Yu; Madeleine Helliwell; James Raftery; Michael Turner

doi:10.1039/C6OB00885B

Alkyl Substituted [2.2]Paracyclophane-‐1,9-‐dienes

Benjamin Lidster, Dharam Kumar, Andrew Spring, Chin Yu, Madeleine Helliwell, James Raftery, Michael Turner

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Abstract

2.2]Paracyclophane-1,9-dienes substituted with n-octyl chains have been synthesised from the corresponding dithia[3.3]paracyclophanes using a benzyne induced Stevens rearrangement. The use of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate and tetra-n-butylammonium fluoride as the in situ benzyne source gave significantly improved yields over traditional sources of benzyne and enabled the preparation of n-octyl substituted [2.2]paracyclophane-1,9-dienes on a multi-gram scale.

Original language	English
Pages (from-to)	6079-6087
Journal	Organic and Biomolecular Chemistry
Volume	14
Issue number	25
Early online date	1 Jun 2016
DOIs	https://doi.org/10.1039/C6OB00885B
Publication status	Published - 7 Jul 2016

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title = "Alkyl Substituted [2.2]Paracyclophane-‐1,9-‐dienes",

abstract = "2.2]Paracyclophane-1,9-dienes substituted with n-octyl chains have been synthesised from the corresponding dithia[3.3]paracyclophanes using a benzyne induced Stevens rearrangement. The use of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate and tetra-n-butylammonium fluoride as the in situ benzyne source gave significantly improved yields over traditional sources of benzyne and enabled the preparation of n-octyl substituted [2.2]paracyclophane-1,9-dienes on a multi-gram scale.",

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T1 - Alkyl Substituted [2.2]Paracyclophane-‐1,9-‐dienes

AU - Lidster, Benjamin

AU - Kumar, Dharam

AU - Spring, Andrew

AU - Yu, Chin

AU - Helliwell, Madeleine

AU - Raftery, James

AU - Turner, Michael

PY - 2016/7/7

Y1 - 2016/7/7

N2 - 2.2]Paracyclophane-1,9-dienes substituted with n-octyl chains have been synthesised from the corresponding dithia[3.3]paracyclophanes using a benzyne induced Stevens rearrangement. The use of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate and tetra-n-butylammonium fluoride as the in situ benzyne source gave significantly improved yields over traditional sources of benzyne and enabled the preparation of n-octyl substituted [2.2]paracyclophane-1,9-dienes on a multi-gram scale.

AB - 2.2]Paracyclophane-1,9-dienes substituted with n-octyl chains have been synthesised from the corresponding dithia[3.3]paracyclophanes using a benzyne induced Stevens rearrangement. The use of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate and tetra-n-butylammonium fluoride as the in situ benzyne source gave significantly improved yields over traditional sources of benzyne and enabled the preparation of n-octyl substituted [2.2]paracyclophane-1,9-dienes on a multi-gram scale.

U2 - 10.1039/C6OB00885B

DO - 10.1039/C6OB00885B

M3 - Article

SN - 1477-0520

VL - 14

SP - 6079

EP - 6087

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 25

ER -

Alkyl Substituted [2.2]Paracyclophane-­‐1,9-­‐dienes

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Alkyl Substituted [2.2]Paracyclophane-‐1,9-‐dienes