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Reversible [4 + 1]‐Selbstaddition von Alkyl(arylimino)phosphanen und regioselektive Cycloaddition mit ( E )‐ und ( Z )‐Azobenzol
Author(s) -
Niecke Edgar,
Link Manfred,
Nieger Martin
Publication year - 1992
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.19921251203
Subject(s) - cycloaddition , chemistry , regioselectivity , dehydrohalogenation , substituent , alkyl , aryl , azobenzene , medicinal chemistry , stereochemistry , ring (chemistry) , intramolecular force , nuclear magnetic resonance spectroscopy , molecule , catalysis , organic chemistry
Reversible [4 + 1] Selfaddition of Alkyl(arylimino)phosphanes and Regioselective Cycloaddition to ( E )‐ and ( Z )‐Azobenzene Dehydrohalogenation of the amino(chloro)phosphanes RP(Cl)N(H)Aryl ( 1 ; RMe, Et; Aryl = 2,4,6‐Tri‐ tert ‐butylphenyl) affords the corresponding iminophosphanes RP NAryl ( 2 ) which undergo a reversible [4 + 1] selfaddition with participation of the aryl substituent to form 3,3a‐Dihydro‐2 H ‐1,2,3λ 5 ‐benzoazadiphospholes 3 . The regioselective cycloaddition of 2b towards ( E )‐ and ( Z )‐azobenzene ( 4a and b ) has been demonstrated in the formation of two different phospholes 6 and 8 which are formed by a [2 + 1] and [4 + 1] cycloaddition reaction of the iminophosphane 2b . The structure of the fiveymembered ring systems 3, 6 and 8 has been elucidated by NMR spectroscopy and single‐crystal X‐ray studies of 3b and 6 .