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Heterotricyclodecane. VII. 2,7‐Dithia‐isotwistan und Derivate
Author(s) -
Ganter C.,
Wigger N.
Publication year - 1972
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19720550219
Subject(s) - chemistry , sulfonium , bicyclic molecule , halide , medicinal chemistry , stereochemistry , organic chemistry , salt (chemistry)
The synthesis of 2,7‐dithia‐isotwistane ( 18 ) and several of its derivatives ( 13 – 17 ) was achieved starting from endo ‐2‐chloro‐9‐thiabicyclo[3.3.1]non‐6‐ene ( 3 ) and using the bicyclic mercaptan 7 as a key intermediate. The isotwistane halides 13 and 14 were treated under reaction conditions suitable for molecular rearrangements involving an epi ‐sulfonium ion ( a ) by neighbouring group participation. However, only isotwistane derivatives were formed ( 13 → 16 , 13 → 17 , 14 → 16 , 14 → 17 ) and no rearranged products with twistane structure could be isolated.