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Dichotomy of Fe + ‐Mediated Sequential Activation of CH/CC Bonds of Aldimines: A Case of Efficient Reaction Control by Chain‐Length Effects Preliminary Communication
Author(s) -
Prüsse Tilmann,
Schwarz Helmut
Publication year - 1990
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.19900730503
Subject(s) - aldimine , chemistry , substrate (aquarium) , stereochemistry , chain (unit) , double bond , metastability , alkyl , surface modification , organic chemistry , catalysis , physics , astronomy , geology , oceanography
The metastable ions of Fe + complexes of aldimines R 1 NCHR 2 exhibit a unique behaviour in that sequential loss of olefin/H 2 follows two distinct pathways: one corresponds to the familiar pattern of double remote functionalization, involving either alkyl chain R 1 and R 2 . In addition, based on labeling studies, evidence is presented demonstrating that the consecutive elimination of C 2 H 4 /H 2 from the Fe + complex of C 6 H 13 NCHC 3 H 7 involves exclusively the C 6 H 13 part of the substrate. These and other Fe + ‐mediated CH/CC bond activations of aldimines are controlled by chain‐length effects, reflecting the preferential formation of metallacyclic intermediates of particular ring sizes.