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Synthesis of a Stable Arenesulfenic Acid Bearing a Bowl‐Shaped Macrobicyclic Cyclophane Skeleton
Author(s) -
Goto Kei,
Tokitoh Norihiro,
Okazaki Renji
Publication year - 1995
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.199511241
Subject(s) - chemistry , sulfoxide , cyclophane , molecule , pyrolysis , solid state , sulfenic acid , carbon skeleton , functional group , polymer chemistry , photochemistry , stereochemistry , organic chemistry , polymer , cysteine , enzyme
A wealth of highly selective reactions may become accessible thanks to the approach described herein: A reactive functional group is placed on the inside of a bowl‐shaped molecular skeleton; in this way, for example, dimerizations can be prevented, but reactions with added small molecules remain possible. The sulfenic acid 1 obtained from the corresponding S ‐butyl sulfoxide by pyrolysis is stable both in the solid state and in solution, and reacts smoothly with methyl propiolate and butanethiol.