1.5- Dithia-2,4,6,8-tetrazocine system

In an attempt to explain the structural dichotomy exhibited by l,5-dithia-2,4,6,8-tetrazocines (see Section 9.26.4.2), a series of calculations have been performed on the system. Several studies have been conducted on the system (1) and derivatives using ab initio and semiempirical methods (84ICA55, 84JA312, 84JA3437, 87JCS(P2)259>. Table 1 summarizes the results of the calculations on the three possible geometries for the parent compound. The l,5-dithia-2,4,6,8-tetrazocine system prefers to adopt a planar lOn-electron monocyclic structure (la). Substituents at the carbon atoms with... 

Only scant reference has been made to model studies on these types of compounds. Thus ab initio (STO-3G) and MNDO calculations on l,5-dithia-2,4,6,8-tetrazocine propound a preference for the lOrc-electron planar monocyclic structure (3) (X = H), and suggest that the bicyclic [l,2,5]thiadiazolo[3,4-c][l,2,5]thiadiazole-2,5-S(IV) (4), an 8n system with a transannular C—C bond could never be the stable structure for this molecule. Hence it is proposed the preparation of... 

Chlorination of bis(dihiethylamino)-l,5-dithia-2,4,6,8-tetrazocine (35) gave bridged system (36) (mp 97-100°C dec.) as orange, moisture sensitive crystals identified by x-ray analysis <85CC655>. 

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