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Generation and Characterization of Transient 3 H ‐Indolium‐methanides
Author(s) -
Döpp Dietrich,
Rehmer Gerd,
Brüggemann Helmut
Publication year - 1988
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.19881210918
Subject(s) - chemistry , trimethylsilyl , dimethyl fumarate , transient (computer programming) , base (topology) , medicinal chemistry , alkoxy group , dimer , stereochemistry , organic chemistry , psychology , mathematical analysis , alkyl , mathematics , psychiatry , multiple sclerosis , computer science , operating system
Abstract Transient 3 H ‐indolium‐methanides 3a – d have been generated from the corresponding 2‐substituted 3 H ‐indoles 1a – d by the N ‐(trimethylsilyl)methylation/desilylation method. 3a,b were trapped by dimethyl maleate and dimethyl fumarate stereospecifically. All ylides add dimethyl ethynedicarboxylate to form 9,9a‐dihydro‐3 H ‐pyrrolo[1,2‐ a ]indoles 11a – d , out of which 11c,d (R = 9a‐alkoxy) readily eliminate the corresponding alkanols to form 12 . In the absence of dipolarophiles, 1a is predominantly transformed into Fischer base 14 , whereas 3b gives rise to an unsymmetrical dimer 16 .