ISSN:
0009-2940
Keywords:
o-Benzoquinone adducts
;
Rearrangement reactions
;
Elimination reactions
;
1,3,2-Diazaphospholidin-1-ium salts
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
o-Benzoquinone Adducts, Rearrangement and Elimination Reactions of 1,1,3-Trimethyl-1,3,2-diazaphospholidin-1-ium SaltsThe 1,1,3-Trimethyl-1,3,2-diazaphospholidin-1-ium Salts X- [1 (X = [Br, Y = NEt2), 2 (X = [BPh4], Y = Me), 3 (X = [BPh4], Y = Ph), 4 (X = [BPh4], Y = NEt2), 5 (X = [BPh4], Y = tBu)] were treated with o-benzoquinones. The reaction of 1 with tetrachloro-o-benzoquinone furnished the spirophosphorane 6 with an intact N → λ5P donor-acceptor interaction. The reaction of 2, 3, and 4 with 3,5-di-tert-butyl-o-benzoquinone furnished [BPh4]- [8 (Y = Me), 9 (Y = Ph), 10 (Y = NEt2)]. The reaction of 5 with 3,5-di-tert-butyl-o-benzoquinone yielded 7 which exhibited no significant N →λ5P donor-acceptor interaction. The rearrangement product 11 was formed in small amounts during the reaction of 5 with tetrachloro-o-benzoquinone; 11 was also prepared by an alternative route. Thermolysis of the 1,1,3-trimethyl-1,3,2-diazaphospholidin-1-ium salts X- [14 (X = Br), 15 (X = I)] in vacuo led, with elimination of methyl halide, to the 1,3,2-diazaphospholidines 16 (X = Br) and 17 (X = I). The salts were characterized by FAB-MS.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19921250407
Permalink