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Reactions of allylzinc bromide with ethynylferrocene derived fluorinated cyclophosphazenes

Authors
Journal
Journal of Organometallic Chemistry
0022-328X
Publisher
Elsevier
Publication Date
Volume
768
Identifiers
DOI: 10.1016/j.jorganchem.2014.06.025
Keywords
  • Fluorophosphazene
  • Ethynylferrocene
  • Terminal Alkenes
  • Allylzinc Bromide
  • Stereospecific

Abstract

Abstract The use of organozinc reagents in the synthesis of terminal alkene derived cyclic halogenated phosphazenes has been explored by the reactions of allylzinc bromide and ethynylferrocene derived fluorophosphazenes. The reaction of monoethynylferrocene derived fluorophosphazene, [(FcCC)(F)PN](PNF2)2 (Fc = ferrocenyl) with allylzinc bromide in 1:6 M ratio resulted in the formation of [FcC(CH2CHCH2)CH(F)PN](PNF2)2 (1) and [FcC(CH2CHCH2)C (CH2CHCH2) (F)PN](PNF2)2 (2) having allyl groups attached to the alkenyl carbon close to the ferrocene moiety. A similar reaction of geminal bisethynylferrocene derived fluorophosphazene, [(FcCC)2PN](PNF2)2 with allylzinc bromide in 1:4 M ratio resulted in the formation of [{FcC(CH2CHCH2)CH}2PN](PNF2)2 (3) while a reaction in 1:14 M ratio resulted in the formation of compound 3 along with the unsymmetrically substituted triallyl derivative, [{FcC(CH2CHCH2)C(CH2CHCH2)} {FcC(CH2CHCH2)CH}PN] (PNF2)2 (4). The new compounds 1–4 were characterized by 1H, 13C{1H}, 31P{1H}, 19F{1H}, IR and HRMS studies. Compounds 1 and 3 have also been structurally characterized by single-crystal X-ray diffraction studies.

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