Synthesis and photochemistry of new chiral keto[3,3]cyclophanes

Ho Suk Shin; Bong Ser Park

doi:10.1002/bkcs.70068

Synthesis and photochemistry of new chiral keto[3,3]cyclophanes

Ho Suk Shin
, Bong Ser Park

Department of Chemistry

Dongguk University

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

Abstract

We have prepared racemates of two new chiral keto[3,3]paracyclophanes and one keto[3,3]metacyclophane by irradiation of the corresponding phenacyl benzoates tethered with a phenol moiety via conformational preorganization enabled by intramolecular charge transfer complex. Their structural properties have been analyzed by X-ray crystallography. The photochemistry of the new cyclophanes has also been examined, in which the beta CO bond cleavage is the major reaction pathway.

Original language	English
Pages (from-to)	1009-1013
Number of pages	5
Journal	Bulletin of the Korean Chemical Society
Volume	46
Issue number	10
DOIs	https://doi.org/10.1002/bkcs.70068
State	Published - Oct 2025

Keywords

[3,3]paracyclophanes
beta CO bond cleavage
intramolecular charge transfer
photochemistry
preorganization

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10.1002/bkcs.70068

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title = "Synthesis and photochemistry of new chiral keto[3,3]cyclophanes",

abstract = "We have prepared racemates of two new chiral keto[3,3]paracyclophanes and one keto[3,3]metacyclophane by irradiation of the corresponding phenacyl benzoates tethered with a phenol moiety via conformational preorganization enabled by intramolecular charge transfer complex. Their structural properties have been analyzed by X-ray crystallography. The photochemistry of the new cyclophanes has also been examined, in which the beta CO bond cleavage is the major reaction pathway.",

keywords = "[3,3]paracyclophanes, beta CO bond cleavage, intramolecular charge transfer, photochemistry, preorganization",

author = "Shin, \{Ho Suk\} and Park, \{Bong Ser\}",

note = "Publisher Copyright: {\textcopyright} 2025 The Author(s). Bulletin of the Korean Chemical Society published by Korean Chemical Society and Wiley-VCH GmbH.",

year = "2025",

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T1 - Synthesis and photochemistry of new chiral keto[3,3]cyclophanes

AU - Shin, Ho Suk

AU - Park, Bong Ser

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N2 - We have prepared racemates of two new chiral keto[3,3]paracyclophanes and one keto[3,3]metacyclophane by irradiation of the corresponding phenacyl benzoates tethered with a phenol moiety via conformational preorganization enabled by intramolecular charge transfer complex. Their structural properties have been analyzed by X-ray crystallography. The photochemistry of the new cyclophanes has also been examined, in which the beta CO bond cleavage is the major reaction pathway.

AB - We have prepared racemates of two new chiral keto[3,3]paracyclophanes and one keto[3,3]metacyclophane by irradiation of the corresponding phenacyl benzoates tethered with a phenol moiety via conformational preorganization enabled by intramolecular charge transfer complex. Their structural properties have been analyzed by X-ray crystallography. The photochemistry of the new cyclophanes has also been examined, in which the beta CO bond cleavage is the major reaction pathway.

KW - [3,3]paracyclophanes

KW - beta CO bond cleavage

KW - intramolecular charge transfer

KW - photochemistry

KW - preorganization

UR - https://www.scopus.com/pages/publications/105018345542

U2 - 10.1002/bkcs.70068

DO - 10.1002/bkcs.70068

M3 - Article

AN - SCOPUS:105018345542

SN - 0253-2964

VL - 46

SP - 1009

EP - 1013

JO - Bulletin of the Korean Chemical Society

JF - Bulletin of the Korean Chemical Society

IS - 10

ER -

Synthesis and photochemistry of new chiral keto[3,3]cyclophanes

Abstract

Keywords

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