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The First Six‐Membered “True” Heterocycle – Hydrogen‐Bond‐Assisted Ladder Formation in a KOCNPS Ring System
Author(s) -
Ly Tuan Q.,
Slawin Alexandra M. Z.,
Woollins J. Derek
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19981002)37:18<2501::aid-anie2501>3.0.co;2-2
Subject(s) - ring (chemistry) , hydrogen bond , bond , chemistry , business , organic chemistry , finance , molecule
A ladder of alternating K 2 S 2 and K 2 O 2 rings exists in K[Ph 2 P(S)NC(O)Ph]⋅MeOH, the first six‐membered “true” heterocycle, in the solid state (see picture). A simple P–N bond‐forming reaction between benzamide and Ph 2 PCl gives the precursor Ph 2 P(S)NHC(O)Ph, from which the potassium salt can be generated by reaction with KO t Bu.