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Alternative Synthesis and Structures of C ‐monoacetylenic Phosphaalkenes
Author(s) -
Orthaber Andreas,
Öberg Elisabet,
Jane Reuben T.,
Ott Sascha
Publication year - 2012
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.201200324
Subject(s) - isomerization , sonogashira coupling , acetylene , chemistry , stereochemistry , crystallography , catalysis , palladium , organic chemistry
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.