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Unexpected Course of Thiocyanation of 1,6‐Methano[10]annulene. Elimination of Thiocyanogen from a Diisothiocyanate
Author(s) -
Neidlein Richard,
Constantinescu Take
Publication year - 1989
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.19891220533
Subject(s) - chemistry , annulene , electrophile , steric effects , adduct , isomerization , halogen , tautomer , methylene , stereochemistry , medicinal chemistry , organic chemistry , alkyl , catalysis
The isolation of the syn , syn ‐adduct 5 in the reaction of 1,6‐methano[10]annulene ( 1 ) with the bulky pseudo‐halogen (SCN) 2 indicates a preferred exo attack of electrophiles on 1 , in spite of a possible steric interference with the methylene bridge. The formation of the unexpected isothiocyanates 4 and 5 is explained in terms of an addition‐isomerization‐elimination sequence. The novel elimination of (SCN) 2 from a diisothiocyanate is investigated.