Hexasulfanyl Analogues of Cyclotriveratrylene

Marc A. Little; Jonathan J. Loughrey; Amedeo Santoro; Malcolm A. Halcrow; Michaele J. Hardie

doi:10.1016/j.tetlet.2014.03.025

Hexasulfanyl Analogues of Cyclotriveratrylene

Marc A. Little, Jonathan J. Loughrey, Amedeo Santoro, Malcolm A. Halcrow^*, Michaele J. Hardie

^*Corresponding author for this work

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

4 Citations (Scopus)

Abstract

The synthesis of four 3,4-di(alkylsulfanyl)benzyl alcohol derivatives is described, in five steps from methyl 3,4-di(hydroxy)benzoate via a Newman-Kwart rearrangement. Incubation of these derivatives in formic acid affords 2,3,7,8,12,13-hexakis(alkylsulfanyl)-10,15-dihydro-5H-tribenzo[a,d,g] cyclononene products, which are hexa-sulfanyl analogues of the well-known supramolecular cavitand host, cyclotriveratrylene (CTV). The yield of this cyclization depends strongly on the alkylsulfanyl substituents present, in the order SMe > SEt ≈ SiPr ≫ SBn. A crystal structure determination of one of the cyclotrimers shows a mode of self-association that is commonly exhibited by CTV itself.

Original language	English
Pages (from-to)	2530-2533
Number of pages	4
Journal	Tetrahedron Letters
Volume	55
Issue number	15
DOIs	https://doi.org/10.1016/j.tetlet.2014.03.025
Publication status	Published - 9 Apr 2014

Keywords

Cavitand
Cyclotriveratrylene
Newman-Kwart rearrangement
Thioether

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2014.03.025

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title = "Hexasulfanyl Analogues of Cyclotriveratrylene",

abstract = "The synthesis of four 3,4-di(alkylsulfanyl)benzyl alcohol derivatives is described, in five steps from methyl 3,4-di(hydroxy)benzoate via a Newman-Kwart rearrangement. Incubation of these derivatives in formic acid affords 2,3,7,8,12,13-hexakis(alkylsulfanyl)-10,15-dihydro-5H-tribenzo[a,d,g] cyclononene products, which are hexa-sulfanyl analogues of the well-known supramolecular cavitand host, cyclotriveratrylene (CTV). The yield of this cyclization depends strongly on the alkylsulfanyl substituents present, in the order SMe > SEt ≈ SiPr ≫ SBn. A crystal structure determination of one of the cyclotrimers shows a mode of self-association that is commonly exhibited by CTV itself.",

keywords = "Cavitand, Cyclotriveratrylene, Newman-Kwart rearrangement, Thioether",

author = "Little, {Marc A.} and Loughrey, {Jonathan J.} and Amedeo Santoro and Halcrow, {Malcolm A.} and Hardie, {Michaele J.}",

year = "2014",

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doi = "10.1016/j.tetlet.2014.03.025",

language = "English",

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journal = "Tetrahedron Letters",

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T1 - Hexasulfanyl Analogues of Cyclotriveratrylene

AU - Little, Marc A.

AU - Loughrey, Jonathan J.

AU - Santoro, Amedeo

AU - Halcrow, Malcolm A.

AU - Hardie, Michaele J.

PY - 2014/4/9

Y1 - 2014/4/9

N2 - The synthesis of four 3,4-di(alkylsulfanyl)benzyl alcohol derivatives is described, in five steps from methyl 3,4-di(hydroxy)benzoate via a Newman-Kwart rearrangement. Incubation of these derivatives in formic acid affords 2,3,7,8,12,13-hexakis(alkylsulfanyl)-10,15-dihydro-5H-tribenzo[a,d,g] cyclononene products, which are hexa-sulfanyl analogues of the well-known supramolecular cavitand host, cyclotriveratrylene (CTV). The yield of this cyclization depends strongly on the alkylsulfanyl substituents present, in the order SMe > SEt ≈ SiPr ≫ SBn. A crystal structure determination of one of the cyclotrimers shows a mode of self-association that is commonly exhibited by CTV itself.

AB - The synthesis of four 3,4-di(alkylsulfanyl)benzyl alcohol derivatives is described, in five steps from methyl 3,4-di(hydroxy)benzoate via a Newman-Kwart rearrangement. Incubation of these derivatives in formic acid affords 2,3,7,8,12,13-hexakis(alkylsulfanyl)-10,15-dihydro-5H-tribenzo[a,d,g] cyclononene products, which are hexa-sulfanyl analogues of the well-known supramolecular cavitand host, cyclotriveratrylene (CTV). The yield of this cyclization depends strongly on the alkylsulfanyl substituents present, in the order SMe > SEt ≈ SiPr ≫ SBn. A crystal structure determination of one of the cyclotrimers shows a mode of self-association that is commonly exhibited by CTV itself.

KW - Cavitand

KW - Cyclotriveratrylene

KW - Newman-Kwart rearrangement

KW - Thioether

UR - http://www.scopus.com/inward/record.url?scp=84897993080&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2014.03.025

DO - 10.1016/j.tetlet.2014.03.025

M3 - Article

AN - SCOPUS:84897993080

SN - 0040-4039

VL - 55

SP - 2530

EP - 2533

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 15

ER -

Hexasulfanyl Analogues of Cyclotriveratrylene

Abstract

Keywords

ASJC Scopus subject areas

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