Cyclodextrin-mediated regioselective photo-Fries reaction of 1-naphthyl phenyl acylates

Smriti Koodanjeri; Ajit R. Pradhan; Lakshmi S. Kaanumalle; V. Ramamurthy

doi:10.1016/S0040-4039(03)00422-2

Cyclodextrin-mediated regioselective photo-Fries reaction of 1-naphthyl phenyl acylates

Smriti Koodanjeri, Ajit R. Pradhan, Lakshmi S. Kaanumalle, V. Ramamurthy

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

18 Scopus citations

Abstract

1-Naphthyl phenyl acylates upon irradiation in solution yield eight products via β-cleavage process. However, excitation of these molecules as included in γ-cyclodextrin results in a single product (>95%). This medium dependent product selectivity is attributed to conformational and translational restrictions enforced on the reactant as well as intermediates by the cyclodextrin cavity.

Original language	English (US)
Pages (from-to)	3207-3210
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	15
DOIs	https://doi.org/10.1016/S0040-4039(03)00422-2
State	Published - Apr 7 2003
Externally published	Yes

Keywords

1-naphthyl phenyl acylates
Cyclodextrin
Photo-Fries reaction
Product control

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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10.1016/S0040-4039(03)00422-2

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title = "Cyclodextrin-mediated regioselective photo-Fries reaction of 1-naphthyl phenyl acylates",

abstract = "1-Naphthyl phenyl acylates upon irradiation in solution yield eight products via β-cleavage process. However, excitation of these molecules as included in γ-cyclodextrin results in a single product (>95%). This medium dependent product selectivity is attributed to conformational and translational restrictions enforced on the reactant as well as intermediates by the cyclodextrin cavity.",

keywords = "1-naphthyl phenyl acylates, Cyclodextrin, Photo-Fries reaction, Product control",

author = "Smriti Koodanjeri and Pradhan, {Ajit R.} and Kaanumalle, {Lakshmi S.} and V. Ramamurthy",

note = "Funding Information: The authors thank the National Science Foundation (CHE-9904187 and CHE-0212042) for support of the research summarized here. V.R. thanks Professor R. G. Weiss for useful discussions at various stages of the project and for providing authentic samples of photoproducts. 8 ",

year = "2003",

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doi = "10.1016/S0040-4039(03)00422-2",

language = "English (US)",

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T1 - Cyclodextrin-mediated regioselective photo-Fries reaction of 1-naphthyl phenyl acylates

AU - Koodanjeri, Smriti

AU - Pradhan, Ajit R.

AU - Kaanumalle, Lakshmi S.

AU - Ramamurthy, V.

N1 - Funding Information: The authors thank the National Science Foundation (CHE-9904187 and CHE-0212042) for support of the research summarized here. V.R. thanks Professor R. G. Weiss for useful discussions at various stages of the project and for providing authentic samples of photoproducts. 8

PY - 2003/4/7

Y1 - 2003/4/7

N2 - 1-Naphthyl phenyl acylates upon irradiation in solution yield eight products via β-cleavage process. However, excitation of these molecules as included in γ-cyclodextrin results in a single product (>95%). This medium dependent product selectivity is attributed to conformational and translational restrictions enforced on the reactant as well as intermediates by the cyclodextrin cavity.

AB - 1-Naphthyl phenyl acylates upon irradiation in solution yield eight products via β-cleavage process. However, excitation of these molecules as included in γ-cyclodextrin results in a single product (>95%). This medium dependent product selectivity is attributed to conformational and translational restrictions enforced on the reactant as well as intermediates by the cyclodextrin cavity.

KW - 1-naphthyl phenyl acylates

KW - Cyclodextrin

KW - Photo-Fries reaction

KW - Product control

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U2 - 10.1016/S0040-4039(03)00422-2

DO - 10.1016/S0040-4039(03)00422-2

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

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ER -