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Heterotricyclodecane. VII. 2,7-Dithia-isotwistan und Derivate

✍ Scribed by C. Ganter; N. Wigger

Publisher
John Wiley and Sons
Year
1972
Tongue
German
Weight
553 KB
Volume
55
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

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.

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