Abstract
AbstractThe sulfines 1–9 in which the o‐positions of the aryl ring A are substituted by methyl groups, have a high rotational barrier about the aryl A to sulfine bond (bond α). Due to this α‐barrier, sulfines 1 and 2 exist as a pair of rotational enantiomers (atropisomerism). The symmetrically substituted sulfines 3,4,7,8 and 9 possess a prochiral centre, viz. the mesityl‐CSO part, provided rotation about bond α is restricted. With rapid rotation about bond α this prochirality disappears (thermally labile prochirality). Chiral lanthanide shift reagents are employed to uncover these chiral properties. The atropisomerism in the sulfines 1 and 2 and the thermally labile prochirality in the sulfines 3,4, 7, 8 and 9 are demonstrated by use of chiral shift reagent. Moreover, chiral shift reagents are successfully used to determine the α‐barrier in the sulfines 3, 4 and 9.
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