Alternative Synthesis and Structures of C‐monoacetylenic Phosphaalkenes |
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Authors: | Andreas Orthaber Elisabet Öberg Reuben T Jane Dr Sascha Ott |
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Institution: | Department of Chemistry‐?ngstr?m Laboratory, Uppsala University, Box 523, SE‐751 20, Uppsala, Sweden |
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Abstract: | An alternative synthesis of C‐monoacetylenic phosphaalkenes trans‐Mes*P=C(Me)(C≡CR) (Mes* = 2, 4, 6‐tBu3Ph, R = Ph, SiMe3) 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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Keywords: | Phosphaalkenes Sonogashira coupling Hay coupling X‐ray crystallography |
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