Tetrahedron: Asymmetry

Design of a new axially chiral molecule by conformational fixation: 2, 6-dithiaspiro [3.3] heptane 2, 6-dioxide and its heavier analogues

Y Naruse, Y Hasegawa, M Araki

文献索引：Naruse, Yuji; Hasegawa, Yousuke; Araki, Motoya Tetrahedron Asymmetry, 2013 , vol. 24, # 13-14 p. 781 - 784

全文：HTML全文

被引用次数: 1

摘要

Abstract We have designed a new axially chiral bis (sulfoxide) molecule with conformational rigidity: 2, 6-dithiaspiro [3.3] heptane 2, 6-dioxide 2a. This molecule has axial asymmetry due to two puckered thietane ring systems. The lone pairs on the sulfur show a strong s- character, which was expected to result in a high barrier to racemization, that is, inversion at the sulfur. We confirmed this prediction by calculations and experimentation. The lone ...