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Synthesis of ortho‐ Phenylenebis(guanidine) Derivatives with Potential Chirality
Author(s) -
Fukuzumi Masahiro,
Nakanishi Waka,
Ishikawa Tsutomu,
Kumamoto Takuya
Publication year - 2014
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201400053
Subject(s) - chemistry , chirality (physics) , guanidine , benzene , stereochemistry , planar chirality , ring (chemistry) , crystal structure , crystallography , medicinal chemistry , axial chirality , salt (chemistry) , catalysis , organic chemistry , enantioselective synthesis , physics , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model , quark
We report the synthesis and potential chirality of ortho ‐phenylenebisguanidines (BGs) with substituents at C(3) and C(6). Guanidinylation of 3,6‐disubstituted benzene‐1,2‐diamines with 2‐chloro‐4,5‐dihydro‐1,3‐dimethyl‐1 H ‐imidazolium chloride gave the corresponding BGs. X‐Ray crystallography showed that the two guanidine moieties occupy different faces of the benzene ring, creating potential chirality, although optical resolution of t Bu‐substituted BG by chiral HPLC failed. However, a methylated acyclic bisguanidinium salt (BGms) was obtained as a chiral crystal with a space group of P 2 1 2 1 2 1 .
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