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Efficient syntheses of polyfunctional nitro compounds using 2‐alkenyl‐substituted methyl 2‐siloxycyclopropanecarboxylates as key building blocks
Author(s) -
Zschiesche Ruth,
Reißig HansUlrich
Publication year - 1988
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198819881210
Subject(s) - umpolung , chemistry , adduct , nitro , cyclopropane , reactivity (psychology) , michael reaction , organic chemistry , polymer chemistry , nucleophile , catalysis , ring (chemistry) , medicine , alkyl , alternative medicine , pathology
Cyclopropane derivatives as 1 are excellent precursors for vinyl ketones like 2 , which can be used as Michael acceptors in reactions with several nitroalkanes. Efficient preparation of trifunctional, tetrafunctional, and pentafunctional compounds is described. Also, nitroalkane adducts like 15 can serve as Michael donor allowing synthesis of adducts 17, 18 , and 19 , respectively. The construction of these polyfunctional systems with differentiated and masked carbonyl groups is analyzed in terms of the concept of reactivity umpolung.