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[3‐Bromo‐2‐lithio‐1‐phenylsulfonylbenzofuran Diisopropyl Ether] 2 and 3‐Fluoro‐2‐lithio‐1‐phenyl‐sulfonylbenzene · Pentamethyldiethylenetriamine : Crystal Structures of Compounds with Lithium and Halogen on Neighboring Carbon Atoms
Author(s) -
Bosold Ferdinand,
Zulauf Peter,
Marsch Michael,
Harms Klaus,
Lohrenz John,
Boche Gernot
Publication year - 1991
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199114551
Subject(s) - chemistry , halogen , lithium (medication) , halide , aryne , ether , crystal structure , medicinal chemistry , crystallography , stereochemistry , polymer chemistry , organic chemistry , medicine , alkyl , endocrinology
The crystal structures and reactivities in solution correlate for the title compounds. The β‐elimination of lithium and halide to the corresponding (hetero)aryne does not occur in the case of bromobenzofuran 1 , in which the CBr bond length is that same as in its nonlithiated counterpart; LiF elimination does occur in compound 2 , whose CF bond is lengthened in comparison to the neutral fluoroarene. This implies that the elimination is structurally predetermined. PMDETA = N , N , N ′, N ″, N ″‐pentamethyldiethylenetriamine.