By Boschke F.L.
Content material: Chapuisat, X. and Jean, Y. Theoretical chemical dynamics: a device in natural chemistry. -- Papousek, D. and Spirko, V. a brand new theoretical examine the inversion challenge in molecules. -- Schneider, H. Ion solvation in combined solvents
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Extra resources for Preparative Organic Chemistry
A special case is the observed substitution with retention as the result of the reaction of N(6)-phenylsulfonyl-4~176 (54) with silver acetate in acetic acid during 9 hrs at 60 ~ which yielded 4~ ~ iodo-adamantane 55 (20% relative to reacted 54) and 4 ~176 mantane 56 (66% relative to reacted 54). ) 36). 2. Substitution and Rearrangement In both cases studied using G 36-adamantanes as starting materials rearranged products were observed where oxonium ions occurred as intermediates, namely on treatment of 4 O(6),80(6)-diiodO-2,6-diOxa-adamantane (5: 2.
Ganter R RiO. k7 k4 R2 R ~00~ H 3 214 215 216 R1 R2 H H Ac H CH 3 CH 3 R 217 218 R H 219 220 CH 3 H CH 3 lic HCl-solution yielded 1-methoxy-4~ (2)-methyl-2,7-dioxa-twistane (220). Model studies on 216 show that in a chair-conformation the methyl group at C(7) would be axial. A boat- or twist-conformation of the six-membered ring, which therefore seems much more likely, is a necessary condition for the ring closure in the case of a twistane-derivative. )]. , was nevertheless successful by applying the following route: according to a procedure by Inhoffen et al.
8. 1. Pathway F (G 15 ~ G 23) 58) Olefin amination of the bicyclic unsaturated secondary amine 204 with mercuric acetate in dimethyl sulfoxide yielded up to 85% of the 10s(7)-acetoxy-2-aza-7-thia41 C. Ganter RN . // R 204 205 R cH 3 CH 3 206 20 7 H H isotwistane 206, whereas by analogous reaction of the bicyclic primary amine 205 the corresponding isotwistane 207 was formed only in a moderate yield. 2. Pathway I (G 18 -+ G 26) s8) Cyclization of the bicyclic bromo-amine 208 in 1,2-dichloroethane in the presence of solid Na2CO3 yielded over 90% of the 10N(2)-bromo-isotwistane 209.
Preparative Organic Chemistry by Boschke F.L.