Alternative Synthesis and Structures of C-monoacetylenic Phosphaalkenes

An alternative synthesis of C-monoacetylenic phosphaalkenes trans-Mes*P=C(Me)(C≡CR) (Mes* = 2, 4, 6-(t)Bu(3)Ph, R = Ph, SiMe(3)) from C-bromophosphaalkenes cis-Mes*P=C(Me)Br using standard Sonogashira coupling conditions is described. Crystallographic studies confirm cis-trans isomerization of the P...

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Autores principales: Orthaber, Andreas, Öberg, Elisabet, Jane, Reuben T, Ott, Sascha
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY-VCH Verlag 2012
Materias:
Articles
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4456767/
https://www.ncbi.nlm.nih.gov/pubmed/26063932
http://dx.doi.org/10.1002/zaac.201200324
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author Orthaber, Andreas
Öberg, Elisabet
Jane, Reuben T
Ott, Sascha
author_facet Orthaber, Andreas
Öberg, Elisabet
Jane, Reuben T
Ott, Sascha
author_sort Orthaber, Andreas
collection PubMed
description An alternative synthesis of C-monoacetylenic phosphaalkenes trans-Mes*P=C(Me)(C≡CR) (Mes* = 2, 4, 6-(t)Bu(3)Ph, R = Ph, SiMe(3)) from C-bromophosphaalkenes cis-Mes*P=C(Me)Br using standard Sonogashira coupling conditions is described. Crystallographic studies confirm cis-trans isomerization of the P=C double bond during Pd-catalyzed cross coupling, leading exclusively to trans-acetylenic phosphaalkenes. Crystallographic studies of all synthesized compounds reveal the extend of π-conjugation over the acetylene and P=C π-systems.
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spelling pubmed-44567672015-06-08 Alternative Synthesis and Structures of C-monoacetylenic Phosphaalkenes Orthaber, Andreas Öberg, Elisabet Jane, Reuben T Ott, Sascha Z Anorg Allg Chem Articles An alternative synthesis of C-monoacetylenic phosphaalkenes trans-Mes*P=C(Me)(C≡CR) (Mes* = 2, 4, 6-(t)Bu(3)Ph, R = Ph, SiMe(3)) from C-bromophosphaalkenes cis-Mes*P=C(Me)Br using standard Sonogashira coupling conditions is described. Crystallographic studies confirm cis-trans isomerization of the P=C double bond during Pd-catalyzed cross coupling, leading exclusively to trans-acetylenic phosphaalkenes. Crystallographic studies of all synthesized compounds reveal the extend of π-conjugation over the acetylene and P=C π-systems. WILEY-VCH Verlag 2012-11 2012-10-09 /pmc/articles/PMC4456767/ /pubmed/26063932 http://dx.doi.org/10.1002/zaac.201200324 Text en Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
spellingShingle Articles
Orthaber, Andreas
Öberg, Elisabet
Jane, Reuben T
Ott, Sascha
Alternative Synthesis and Structures of C-monoacetylenic Phosphaalkenes
title Alternative Synthesis and Structures of C-monoacetylenic Phosphaalkenes
title_full Alternative Synthesis and Structures of C-monoacetylenic Phosphaalkenes
title_fullStr Alternative Synthesis and Structures of C-monoacetylenic Phosphaalkenes
title_full_unstemmed Alternative Synthesis and Structures of C-monoacetylenic Phosphaalkenes
title_short Alternative Synthesis and Structures of C-monoacetylenic Phosphaalkenes
title_sort alternative synthesis and structures of c-monoacetylenic phosphaalkenes
topic Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4456767/
https://www.ncbi.nlm.nih.gov/pubmed/26063932
http://dx.doi.org/10.1002/zaac.201200324
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