Synthesis of [1.1.1.1]Metacyclophane Macrocycle

Andrzej Rajca; Raghavakaimal Padmakumar; Donald J. Smithhisler; Shailesh R. Desai; Charles R. Ross; John J. Stezowski

doi:10.1021/jo00104a027

Synthesis of [1.1.1.1]Metacyclophane Macrocycle

Andrzej Rajca, Raghavakaimal Padmakumar, Donald J. Smithhisler, Shailesh R. Desai, Charles R. Ross, John J. Stezowski

Chemistry

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

19 Scopus citations

Abstract

Additions of organodilithium reagents to dialdehydes allow for construction of [1.1.1.1]metacyclophane macrocycle in ∼40% yield in the ring forming step, without resort to standard high dilution techniques. The present methodology is complementary to the conventional condensations leading to phenol- and resorcinol-based cyclotetramers.

Original language	English (US)
Pages (from-to)	7701-7703
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	59
Issue number	25
DOIs	https://doi.org/10.1021/jo00104a027
State	Published - Dec 1 1994

ASJC Scopus subject areas

Organic Chemistry

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title = "Synthesis of [1.1.1.1]Metacyclophane Macrocycle",

abstract = "Additions of organodilithium reagents to dialdehydes allow for construction of [1.1.1.1]metacyclophane macrocycle in ∼40% yield in the ring forming step, without resort to standard high dilution techniques. The present methodology is complementary to the conventional condensations leading to phenol- and resorcinol-based cyclotetramers.",

author = "Andrzej Rajca and Raghavakaimal Padmakumar and Smithhisler, {Donald J.} and Desai, {Shailesh R.} and Ross, {Charles R.} and Stezowski, {John J.}",

year = "1994",

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doi = "10.1021/jo00104a027",

language = "English (US)",

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journal = "Journal of Organic Chemistry",

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T1 - Synthesis of [1.1.1.1]Metacyclophane Macrocycle

AU - Rajca, Andrzej

AU - Padmakumar, Raghavakaimal

AU - Smithhisler, Donald J.

AU - Desai, Shailesh R.

AU - Ross, Charles R.

AU - Stezowski, John J.

PY - 1994/12/1

Y1 - 1994/12/1

N2 - Additions of organodilithium reagents to dialdehydes allow for construction of [1.1.1.1]metacyclophane macrocycle in ∼40% yield in the ring forming step, without resort to standard high dilution techniques. The present methodology is complementary to the conventional condensations leading to phenol- and resorcinol-based cyclotetramers.

AB - Additions of organodilithium reagents to dialdehydes allow for construction of [1.1.1.1]metacyclophane macrocycle in ∼40% yield in the ring forming step, without resort to standard high dilution techniques. The present methodology is complementary to the conventional condensations leading to phenol- and resorcinol-based cyclotetramers.

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JF - Journal of Organic Chemistry

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ER -

Synthesis of [1.1.1.1]Metacyclophane Macrocycle

Abstract

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