Chiral conjoined cavitands

Jacob L. Irwin; David J. Sinclair; Alison J. Edwards; Michael S. Sherburn

doi:10.1071/CH03299

Chiral conjoined cavitands

Jacob L. Irwin, David J. Sinclair, Alison J. Edwards, Michael S. Sherburn^*

^*Corresponding author for this work

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

4 Citations (Scopus)

Abstract

Tetrabromocavitand bowls are converted into rim-connected hexabromodimers in one step in 17-22% yields by oxidative coupling of higher order arylcuprates. ¹H NMR and single crystal X-ray analyses of the rim-connected dimers reveal a conformationally restricted structure in which the rims of the two cavitand bowls describe planes angled at 78.8° to one another. Each of the two bowl cavities are occupied by a guest, in addition to being partially occluded by a portion of the complementary bowl rim. These new host compounds exhibit a very unusual form of enantioisomerism.

Original language	English
Pages (from-to)	339-343
Number of pages	5
Journal	Australian Journal of Chemistry
Volume	57
Issue number	4
DOIs	https://doi.org/10.1071/CH03299
Publication status	Published - 2004

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10.1071/CH03299

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title = "Chiral conjoined cavitands",

abstract = "Tetrabromocavitand bowls are converted into rim-connected hexabromodimers in one step in 17-22\% yields by oxidative coupling of higher order arylcuprates. 1H NMR and single crystal X-ray analyses of the rim-connected dimers reveal a conformationally restricted structure in which the rims of the two cavitand bowls describe planes angled at 78.8° to one another. Each of the two bowl cavities are occupied by a guest, in addition to being partially occluded by a portion of the complementary bowl rim. These new host compounds exhibit a very unusual form of enantioisomerism.",

author = "Irwin, \{Jacob L.\} and Sinclair, \{David J.\} and Edwards, \{Alison J.\} and Sherburn, \{Michael S.\}",

year = "2004",

doi = "10.1071/CH03299",

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volume = "57",

pages = "339--343",

journal = "Australian Journal of Chemistry",

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T1 - Chiral conjoined cavitands

AU - Irwin, Jacob L.

AU - Sinclair, David J.

AU - Edwards, Alison J.

AU - Sherburn, Michael S.

PY - 2004

Y1 - 2004

N2 - Tetrabromocavitand bowls are converted into rim-connected hexabromodimers in one step in 17-22% yields by oxidative coupling of higher order arylcuprates. 1H NMR and single crystal X-ray analyses of the rim-connected dimers reveal a conformationally restricted structure in which the rims of the two cavitand bowls describe planes angled at 78.8° to one another. Each of the two bowl cavities are occupied by a guest, in addition to being partially occluded by a portion of the complementary bowl rim. These new host compounds exhibit a very unusual form of enantioisomerism.

AB - Tetrabromocavitand bowls are converted into rim-connected hexabromodimers in one step in 17-22% yields by oxidative coupling of higher order arylcuprates. 1H NMR and single crystal X-ray analyses of the rim-connected dimers reveal a conformationally restricted structure in which the rims of the two cavitand bowls describe planes angled at 78.8° to one another. Each of the two bowl cavities are occupied by a guest, in addition to being partially occluded by a portion of the complementary bowl rim. These new host compounds exhibit a very unusual form of enantioisomerism.

UR - https://www.scopus.com/pages/publications/1942468734

U2 - 10.1071/CH03299

DO - 10.1071/CH03299

M3 - Article

SN - 0004-9425

VL - 57

SP - 339

EP - 343

JO - Australian Journal of Chemistry

JF - Australian Journal of Chemistry

IS - 4

ER -

Chiral conjoined cavitands

Abstract

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