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Reaction of Dihydrodiazaphosphinines with Acetylenic Diesters: A Direct Synthesis of the λ 5 ‐Diazaphosphaazulene Skeleton
Author(s) -
Barluenga José,
Tomás Miguel,
Bieger Klaus,
GarcíaGranda Santiago,
SantiagoGarcía Rafael
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(199807)1998:7<1425::aid-ejoc1425>3.0.co;2-0
Subject(s) - tetracyanoethylene , chemistry , dimethyl acetylenedicarboxylate , electrophile , reactivity (psychology) , acetylene , adduct , cycloaddition , acetylenedicarboxylate , organic chemistry , medicinal chemistry , stereochemistry , catalysis , medicine , alternative medicine , pathology
1,2‐Dihydro‐1,3,2‐diazaphosphinine 2 reacts with acetylene‐dicarboxylic acid esters to give chemoselectively the adducts 5 or 6a , b , depending on the reaction conditions. Compound 6a is alternatively synthesized by treatment of equimolecular amounts of the previously described monoadduct 3 ( 3′ ) and dimethyl acetylenedicarboxylate. A reaction pathway is proposed based primarily on i) the isolation and characterization of intermediate 8 ( 8′ ) and ii) the reactivity of 3 ( 3′ ) towards electrophiles, in particular with tetracyanoethylene (compound 10 ).