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Dichlorocyclopropanation, epoxidation, and subsequent reactions of isotetralin derivatives
Author(s) -
Hashem Md. Abul,
MarschallWeyerstahl Helga,
Weyerstahl Peter
Publication year - 1986
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19861190209
Subject(s) - chemistry , epoxide , diol , lactone , adduct , ring (chemistry) , stereochemistry , medicinal chemistry , organic chemistry , catalysis
Reaction of excess CCl 2 with isotetralin ( 1 ) gives a separable mixture of bis‐ and tris‐adducts 3 – 6 , where 6 exhibits syn ‐standing dichlorocyclopropanes at a six‐membered ring. – Epoxidation of 2a and b furnishes the symmetrical diepoxides 7a and b . With BuLi/CO 2 , 7b afforded the α‐bromo lactone 10 . – From 3 the epoxide 8 is formed which is cleaved to give the diol 11 . – The epoxide 9a proves the anti ‐structure of 4 . – LiAlH 4 reduction of 3 leads by exo ‐attack mainly to a separable mixture of 13 and 14 .