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Syntheses and Structural Properties of Cyclic Tetrathiadiynes
Author(s) -
Benisch Christoph,
Bethke Sabine,
Gleiter Rolf,
Oeser Thomas,
Pritzkow Hans,
Rominger Frank
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200007)2000:13<2479::aid-ejoc2479>3.0.co;2-9
Subject(s) - chemistry , dilithium , moiety , acetylide , trimethylsilyl , cyclopentane , ring (chemistry) , stereochemistry , torsion (gastropod) , conformational isomerism , twist , crystallography , computational chemistry , molecule , medicinal chemistry , organic chemistry , medicine , ion , deprotonation , geometry , surgery , mathematics
Abstract The four‐component cyclization of dilithium acetylide with dithiocyanatoalkanes yielded the hitherto unknown tetrathiacyclodiynes 34 , 38 , 41 , and 43 in moderate yields. The use of the trimethylsilyl protecting group allowed a more efficient and flexible stepwise approach with good yields. The resulting tetrathiacyclodiynes 25 − 44 were investigated by X‐ray analysis. For ring systems with a twist‐chair conformation the torsion angle between the CH 2 −S σ‐bonds of the CH 2 −S−C≡C−S−CH 2 moiety adopts values between 75° and 110°. These values are due to electronic effects, as shown by HF/6‐31G* calculations.