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Synthesis of cis , cis , cis , cis ‐[5.5.5.5]‐1‐Azafenestrane
Author(s) -
Denmark Scott E.,
Kramps Laurenz A.,
Montgomery Justin I.
Publication year - 2002
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20021104)41:21<4122::aid-anie4122>3.0.co;2-w
Subject(s) - tetracoordinate , borane , chemistry , ring (chemistry) , carbon fibers , crystallography , asymmetric carbon , molecule , atom (system on chip) , stereochemistry , materials science , organic chemistry , computer graphics (images) , optically active , composite number , computer science , composite material , planar , embedded system , catalysis
To provide an opportunity for X‐ray analysis of an unsubstituted fenestrane, one of the ring‐fusion carbon atoms was replaced with a nitrogen atom to facilitate salt formation; the key strategic step to the first 1‐azafenestrane (see scheme) involves the tandem [4+2]/[3+2] cycloaddition of a nitrocyclopentene with butyl vinyl ether. The adduct with borane provided crystals suitable for X‐ray analysis, which revealed the planar deformation of the central carbon atom to be modest (116.1 and 116.6°).