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Synthesis, Structure, and Double Olefin Extrusion of All Three Diastereomers of 2,2,6,6‐Tetrakis(4‐chlorophenyl)‐3,7‐dimethyl‐4‐phenyl‐1,5‐dioxa‐4λ 5 ‐phosphaspiro[3.3]heptane
Author(s) -
Kawashima Takayuki,
Okazaki Rei,
Okazaki Renji
Publication year - 1997
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199725001
Subject(s) - diastereomer , steric effects , chemistry , trigonal bipyramidal molecular geometry , tetragonal crystal system , olefin fiber , thermal decomposition , crystallography , cis–trans isomerism , stereochemistry , decomposition , crystal structure , medicinal chemistry , catalysis , organic chemistry
A distorted tetragonal‐pyramidal structure is adopted by the trans‐trans diastereomer of the spirophos‐phorane 1 . In contrast, the cis‐trans isomer displays a distorted trigonal‐bipyramidal structure. These two as well as the cis‐cis diastereomer were synthesized as stable crystals by taking advantage of electronic and steric effects of the methyl groups in the 3‐ and 7‐positions. Interestingly, thermolysis of 1 gave two molar equivalents of Ar 2 CCHMe. Ar = 4‐ClC 6 H 4 .