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Conformation in the Solid State and in Solution of 3,3′(4 H ,4′ H )‐Spirobi[2 H ‐1,5‐benzodioxepin]
Author(s) -
Grochowski Jacek,
Rutkowska Maria,
Rys Barbara,
Serda Pavel,
Snatzke Günther
Publication year - 1992
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19921250809
Subject(s) - chemistry , menthol , enantiomer , absolute configuration , solid state , stereochemistry , molecule , crystallography , organic chemistry
The “spiro‐coplanar” conformation of 6,6′‐methoxycarbonyl‐3,3′(4 H ,4′ H )‐spirobi[2 H ‐1,5‐benzodioxepin] ( 1b ) and the 3 P configuration of the corresponding menthol ester 1c have been determined from chiroptical data by application of the exciton theory. The solid‐state conformation of the central part of the menthol ester molecule is “spiro‐coplanar”, too, with nearly D 2 symmetry. The menthol moieties have chair conformations, and the absolute configurations at their chiral centers have been assigned using enantiomer‐sensitive Bijvoet pairs; they are in agreement with the known absolute configuration of menthol.