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Heterotricyclodecane XIX. Umlagerungen von 4,8‐disubstituierten 2,6‐Dioxa‐ und 2‐Oxa‐6‐aza‐adamantanen zu 4,10‐disubstituierten 2,7‐Dioxa‐ und 2‐Oxa‐7‐aza‐isotwistanen sowie ‐twistanen
Author(s) -
Ackermann Peter,
Portmann Robert Ernst,
Ganter Camille
Publication year - 1976
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.19760590727
Subject(s) - chemistry , stereochemistry , medicinal chemistry
Rearrangements of 4,8‐disubstituted 2,6‐dioxa‐ and 2‐oxa‐6‐aza‐adamantanes to 4,10‐disubstituted 2,7‐dioxa‐ and 2‐oxa‐7‐aza‐isotwistanes as well as ‐twistanes. Substitutions and rearrangements involving neighboring group participation starting from 4,8‐diiodo‐2,6‐dioxa‐ and 4,8‐diiodo‐2‐oxa‐6‐aza‐adamantanes ( 5 and 6, 12 and 48 , resp.) were studied, yielding 4,8‐disubstituted 2,6‐dioxa‐ and 2‐oxa‐6‐aza‐adamantanes ( 7, 9, 39, 42 and 13, 15, 50, 52 , resp.), 4,10‐disubstituted 2,7‐dioxa‐ and 2‐oxa‐7‐aza‐isotwistanes ( 8, 10, 41, 43 and 14, 16, 51, 53 , resp.) and corresponding‐twistanes ( 11 and 17 , resp.).