Pnictogen-directed synthesis of discrete disulfide macrocycles

Mary S. Collins; Matthew E. Carnes; Aaron C. Sather; Orion B. Berryman; Lev N. Zakharov; Simon J. Teat; Darren W. Johnson

doi:10.1039/c3cc43524e

Pnictogen-directed synthesis of discrete disulfide macrocycles

Mary S. Collins, Matthew E. Carnes, Aaron C. Sather, Orion B. Berryman, Lev N. Zakharov, Simon J. Teat, Darren W. Johnson

Chemistry and Biochemistry

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

17 Scopus citations

Abstract

Cyclic disulfide macrocycles were rapidly synthesized cleanly and selectively from rigid dithiols via oxidation with iodine when activated by pnictogen additives (As and Sb). Macrocycles were confirmed by ¹H-NMR spectroscopy and X-ray crystallography. A p-xylyl-based disulfide trimer and tetramer crystallized in hollow, stacked columns stabilized by intermolecular, sulfur⋯sulfur close contacts.

Original language	English
Pages (from-to)	6599-6601
Number of pages	3
Journal	Chemical Communications
Volume	49
Issue number	59
DOIs	https://doi.org/10.1039/c3cc43524e
State	Published - Jun 27 2013

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title = "Pnictogen-directed synthesis of discrete disulfide macrocycles",

abstract = "Cyclic disulfide macrocycles were rapidly synthesized cleanly and selectively from rigid dithiols via oxidation with iodine when activated by pnictogen additives (As and Sb). Macrocycles were confirmed by 1H-NMR spectroscopy and X-ray crystallography. A p-xylyl-based disulfide trimer and tetramer crystallized in hollow, stacked columns stabilized by intermolecular, sulfur⋯sulfur close contacts.",

author = "Collins, \{Mary S.\} and Carnes, \{Matthew E.\} and Sather, \{Aaron C.\} and Berryman, \{Orion B.\} and Zakharov, \{Lev N.\} and Teat, \{Simon J.\} and Johnson, \{Darren W.\}",

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language = "English",

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T1 - Pnictogen-directed synthesis of discrete disulfide macrocycles

AU - Collins, Mary S.

AU - Carnes, Matthew E.

AU - Sather, Aaron C.

AU - Berryman, Orion B.

AU - Zakharov, Lev N.

AU - Teat, Simon J.

AU - Johnson, Darren W.

PY - 2013/6/27

Y1 - 2013/6/27

N2 - Cyclic disulfide macrocycles were rapidly synthesized cleanly and selectively from rigid dithiols via oxidation with iodine when activated by pnictogen additives (As and Sb). Macrocycles were confirmed by 1H-NMR spectroscopy and X-ray crystallography. A p-xylyl-based disulfide trimer and tetramer crystallized in hollow, stacked columns stabilized by intermolecular, sulfur⋯sulfur close contacts.

AB - Cyclic disulfide macrocycles were rapidly synthesized cleanly and selectively from rigid dithiols via oxidation with iodine when activated by pnictogen additives (As and Sb). Macrocycles were confirmed by 1H-NMR spectroscopy and X-ray crystallography. A p-xylyl-based disulfide trimer and tetramer crystallized in hollow, stacked columns stabilized by intermolecular, sulfur⋯sulfur close contacts.

UR - https://www.scopus.com/pages/publications/84879773265

U2 - 10.1039/c3cc43524e

DO - 10.1039/c3cc43524e

M3 - Article

C2 - 23770675

AN - SCOPUS:84879773265

SN - 1359-7345

VL - 49

SP - 6599

EP - 6601

JO - Chemical Communications

JF - Chemical Communications

IS - 59

ER -

Pnictogen-directed synthesis of discrete disulfide macrocycles

Abstract

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