Directed lithiation of some chroman-4-ols

Richard J. Bethune; Christopher D. Gabbutt; Stéphane G R Guinot; John D. Hepworth; B. Mark Heron

doi:10.1039/P19940001925

Directed lithiation of some chroman-4-ols

Richard J. Bethune, Christopher D. Gabbutt, Stéphane G R Guinot, John D. Hepworth, B. Mark Heron

University of Lancashire

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

10 Citations (Scopus)

Abstract

Directed lithiation of chroman-4-ols occurs predominantly at C-5 under kinetic control, but at C-8 at higher temperatures. Dehydration and oxidation of the products provides viable routes to 5-substituted 2H-chromenes and chroman-4-ones, respectively. The chroman-4-ones have been converted into novel pyrano[4,3,2-de]phthalazines. 2,2,5,7-Tetramethylchroman-4-ol is preferentially lithiated at the 5-methyl group and leads to the pyrano[2,3,4-de] [1]benzopyran system.

Original language	English
Pages (from-to)	1925-1933
Number of pages	9
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	14
DOIs	https://doi.org/10.1039/P19940001925
Publication status	Published - 1 Dec 1994
Externally published	Yes

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title = "Directed lithiation of some chroman-4-ols",

abstract = "Directed lithiation of chroman-4-ols occurs predominantly at C-5 under kinetic control, but at C-8 at higher temperatures. Dehydration and oxidation of the products provides viable routes to 5-substituted 2H-chromenes and chroman-4-ones, respectively. The chroman-4-ones have been converted into novel pyrano[4,3,2-de]phthalazines. 2,2,5,7-Tetramethylchroman-4-ol is preferentially lithiated at the 5-methyl group and leads to the pyrano[2,3,4-de] [1]benzopyran system.",

author = "Bethune, \{Richard J.\} and Gabbutt, \{Christopher D.\} and Guinot, \{St{\'e}phane G R\} and Hepworth, \{John D.\} and Heron, \{B. Mark\}",

year = "1994",

month = dec,

day = "1",

doi = "10.1039/P19940001925",

language = "English",

pages = "1925--1933",

journal = "Journal of the Chemical Society, Perkin Transactions 1",

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T1 - Directed lithiation of some chroman-4-ols

AU - Bethune, Richard J.

AU - Gabbutt, Christopher D.

AU - Guinot, Stéphane G R

AU - Hepworth, John D.

AU - Heron, B. Mark

PY - 1994/12/1

Y1 - 1994/12/1

N2 - Directed lithiation of chroman-4-ols occurs predominantly at C-5 under kinetic control, but at C-8 at higher temperatures. Dehydration and oxidation of the products provides viable routes to 5-substituted 2H-chromenes and chroman-4-ones, respectively. The chroman-4-ones have been converted into novel pyrano[4,3,2-de]phthalazines. 2,2,5,7-Tetramethylchroman-4-ol is preferentially lithiated at the 5-methyl group and leads to the pyrano[2,3,4-de] [1]benzopyran system.

AB - Directed lithiation of chroman-4-ols occurs predominantly at C-5 under kinetic control, but at C-8 at higher temperatures. Dehydration and oxidation of the products provides viable routes to 5-substituted 2H-chromenes and chroman-4-ones, respectively. The chroman-4-ones have been converted into novel pyrano[4,3,2-de]phthalazines. 2,2,5,7-Tetramethylchroman-4-ol is preferentially lithiated at the 5-methyl group and leads to the pyrano[2,3,4-de] [1]benzopyran system.

UR - https://www.scopus.com/pages/publications/37049081020

U2 - 10.1039/P19940001925

DO - 10.1039/P19940001925

M3 - Article

AN - SCOPUS:37049081020

SN - 1472-7781

SP - 1925

EP - 1933

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 14

ER -

Directed lithiation of some chroman-4-ols

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