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Novel Solid‐State Synthesis of Polyfunctionalized 3,9‐Diazatetraasteranes
Author(s) -
Hilgeroth Andreas,
Baumeister Ute,
Heinemann Frank W.
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199806)1998:6<1213::aid-ejoc1213>3.0.co;2-u
Subject(s) - chemistry , crystal structure , ring (chemistry) , monomer , derivative (finance) , solid state , crystallography , stereochemistry , double bond , crystal (programming language) , polymer chemistry , organic chemistry , polymer , computer science , financial economics , programming language , economics
Upon irradiation, crystalline 4‐methoxyphenyl‐1,4‐dihy‐dropyridines 1 undergo nearly quantitative [2+2]cyclo‐addition to form, via the ring‐open intermediates 2 , the centrosymmetric, polyfunctionalized 3,9‐diazatetraasteranes 3 . The centrosymmetric character of 3 was confirmed by 1 H NMR spectral data as well as by X‐ray crystal structure analysis. The dimerization reactions prove to be topochemically controlled by the nearest distance between potentially reacting double bonds, as well as by the conformationally determined packing restraints. This latter factor is shown by the X‐ray crystal structure analysis of one dimerizing and one photostable derivative of the monomers 1 .