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Preparation and Structures of Cyclic Tetrathiadienes and Tetrathiaenynes
Author(s) -
Staeb Tobias H.,
Gleiter Rolf,
Rominger Frank
Publication year - 2002
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(200208)2002:16<2815::aid-ejoc2815>3.0.co;2-9
Subject(s) - chemistry , zigzag , crystallography , molecule , hydride , solid state , stereochemistry , x ray crystallography , hydrocarbon , diffraction , organic chemistry , metal , physics , geometry , mathematics , optics
Through the use of diisobutylaluminium hydride (DIBAH) we were able to reduce selectively the triple bond(s) of the following cyclic diynes: 1,4,7,10‐tetrathiacyclodeca‐2,8‐diyne ( 1 ), 1,4,8,11‐tetrathiacyclotetradeca‐2,9‐diyne ( 2 ), 1,4,9,12‐tetrathiacyclohexadeca‐2,10‐diyne ( 3 ), 1,4,10,13‐tetrathiacyclooctadeca‐2,11‐diyne ( 4 ), 1,4,11,14‐tetrathiacycloeicosa‐2,12‐diyne ( 5 ), 1,4,8,11‐tetrathiacycloheptadeca‐2,9‐diyne ( 6 ), and 7,16‐dioxa‐1,4,10,13‐tetrathiacyclooctadeca‐2,11‐diyne ( 7 ). The resulting cyclic enynes 8 − 14 and cyclic dienes 15 − 20 were isolated and characterized by their analytical data. In the cases of 8 , 10 , 11 , 14 , and 15 − 20 we were able to isolate single crystals, which were investigated by X‐ray diffraction. For all molecular structures we found stair‐like conformations. These shapes of the molecules were traced back to the zigzag arrangements of the hydrocarbon chains and the rigid building units (S−CH=CH−S) and/or (S−C≡C−S). In the solid‐state forms of 11 , 16 , 17 , and 19 we encountered columnar structures caused by close contacts between sulfur centers of neighboring rings. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)