📘 ❞ New stabilising groups for lateral lithiation of ortho-cresol derivatives ❝ كتاب

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█ _ 0 حصريا كتاب ❞ New stabilising groups for lateral lithiation of ortho cresol derivatives ❝ 2025 derivatives: orthocresol من كتب علمية James A Wilkinson New derivatives and a new route to 2 substituted chromans James Wilkinson *, Eun Ang Raiber, Sylvie Ducki Centre Molecular Drug Design, Biosciences Research Institute, Cockcroft Building, University Salford, Salford M5 4WT, UK a r t i c l e n f o Article history: Received 30 January 2008 Received in revised form 4 April 2008 Accepted 24 2008 Available online 29 2008 Keywords: Lateral lithiation Alkylation ortho Cresol Chromans a b s t 2 (2 Methoxyethoxy) toluene and dimethylaminoethoxy) have been lithiated using sec BuLi under variety conditions the laterally species trapped with electrophiles, including but 1 ene oxide, leading synthesis ethylchroman 2008 Elsevier Ltd All rights reserved 1 Introduction Lateral is an important methodology organic Lateral benzenoid aromatics requires stabilising group capable either delocalising negative charge or stabilising organolithium by coordination Oxygen based stabilising groups placed position used for a number lithiations but are problematic case of simple The methoxy group requires superbase effect deprotonation methoxymethyl group gives exclusive (Scheme 1) 3 In previous work on diarylmethane we used the methoxyethoxy efficient This led us to investigate use same as potentially more efficient stabiliser We recently reported reactions orthocresol derivatives both dimethylaminoethoxy stabilising 5 Here, report full results of these investigations مجاناً PDF اونلاين الطريقة العلمية أو المنهج العلمي الثقافة عبارة عن مجموعة التقنيات والطرق المصممة لفحص الظواهر والمعارف المكتشفة المراقبة حديثا من ضمن محتويات القسم : العلماء‏ , أحيائية,‏ بيئية لا خيالية,‏ رياضيات,‏ طب‏, علم والكثير

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New stabilising groups for lateral lithiation of ortho-cresol derivatives
كتاب

New stabilising groups for lateral lithiation of ortho-cresol derivatives

New stabilising groups for lateral lithiation of ortho-cresol derivatives
كتاب

New stabilising groups for lateral lithiation of ortho-cresol derivatives

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عن كتاب New stabilising groups for lateral lithiation of ortho-cresol derivatives:
New stabilising groups for lateral lithiation of orthocresol derivatives من كتب علمية
James A. Wilkinson

New stabilising groups for lateral lithiation of ortho-cresol derivatives
and a new route to 2-substituted chromans
James A. Wilkinson *, Eun-Ang Raiber, Sylvie Ducki
Centre for Molecular Drug Design, Biosciences Research Institute, Cockcroft Building, University of Salford, Salford M5 4WT, UK
a r t i c l e i n f o
Article history:
Received 30 January 2008
Received in revised form 4 April 2008
Accepted 24 April 2008
Available online 29 April 2008
Keywords:
Lateral lithiation
Alkylation
ortho-Cresol
Chromans
a b s t r a c t
2-(2-Methoxyethoxy)-toluene and 2-(2-dimethylaminoethoxy)-toluene have been lithiated using sec-
BuLi under a variety of conditions and the laterally lithiated species trapped with electrophiles, including
but-1-ene oxide, leading to a new synthesis of 2-ethylchroman.
2008 Elsevier Ltd. All rights reserved.
1. Introduction
Lateral lithiation is an important methodology in organic synthesis.
1 Lateral lithiation of benzenoid aromatics requires a stabilising
group capable of either delocalising negative charge or
stabilising an organolithium by coordination.2 Oxygen-based stabilising
groups placed in the ortho-position have been used for
a number of lateral lithiations but are problematic in the case of
simple ortho-cresol derivatives. The methoxy group requires
superbase conditions to effect deprotonation and the methoxymethyl
group gives exclusive ortho-lithiation (Scheme 1).3
In a previous work on diarylmethane derivatives we have used
the methoxyethoxy group in efficient lateral lithiations.4 This led us
to investigate the use of the same group as a potentially more
efficient stabiliser for lateral lithiation of ortho-cresol derivatives.
We have recently reported lateral lithiation reactions of orthocresol
derivatives using both the methoxyethoxy and dimethylaminoethoxy
stabilising groups.5 Here, we report in full the results
of these investigations
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