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Spirocyclization of a Stable Phosphaalkyne with Aluminum Trichloride—Key Reaction for the Production of Triphospha Dewar Benzene Derivatives
Author(s) -
Breit Bernhard,
Bergsträsser Uwe,
Maas Gerhard,
Regitz Manfred
Publication year - 1992
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199210551
Subject(s) - chemistry , benzene , lewis acids and bases , dimethyl sulfoxide , medicinal chemistry , cleavage (geology) , photochemistry , organic chemistry , catalysis , geotechnical engineering , fracture (geology) , engineering
In a highly selective reaction the spirocyclotrimer 2 is formed when the phosphaalkyne 1 is treated with the Lewis acid AlCl 3 . The diphosphet is released when dimethyl sulfoxide (DMSO) is added, and it subsequently rearranges to 1,3,5‐triphospha Dewar benzene by cleavage of the PP bond in the diphosphirene unit. This can be trapped with 1 by a homo–Diels–Alder reaction leading to the formation of the tetraphosphacubane 3 . All these reaction steps are novel.