Mononuclear Schiff base boron halides: Synthesis, characterization, and dealkylation of trimethyl phosphate

Amitabha Mitra, Lauren J. DePue, Jeffrey E. Struss, Bijal P. Patel, Sean Parkin, David A. Atwood

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

A series of mononuclear boron halides of the type LBX2 [LH = N-phenyl-3,5-di-tert-butylsalicylaldimine, X = Cl (2), Br (3)] and LBX [LH 2 = N-(2-hydroxyphenyl)-3,5-di-tert-butylsalicylaldimine, X = Cl (7), Br (8); LH2 = N-(2-hydroxyethyl)-3,5-di-tert-butylsalicylaldimine, X = Cl (9), Br (10); and LH2= N-(3-hydroxypropyl)-3,5-di-tert- butylsalicylaldimine, X = Cl (11), Br (12)] were synthesized from their borate precursors LB(OMe)2 (1) (LH = N-phenyl-3,5-di-tert- butylsalicylaldimine) and LB(OMe) [LH2 = N-(2-hydroxyphenyl)-3,5-di- tert-butylsalicylaldimine (4), N-(2-hydroxyethyl)-3,5-di-tert- butylsalicylaldimine (5), N-(3-hydroxypropyl)-3,5-di-tert-butylsalicylaldimine (6)]. The boron halide compounds were air and moisture sensitive, and upon hydrolysis, compound 7 resulted in the oxobridged compound 13 that contained two seven-membered boron heterocycles. The boron halide compounds dealkylated trimethyl phosphate in stoichiometric reactions to produce methyl halide and unidentified phosphate materials. Compounds 8 and 12 were found to be the most effective dealkylating agents. On reaction with tert-butyl diphenyl phosphinate, compound 8 produced a unique boron phosphinate compound LB(O)OPPh2 (14) containing a terminal phosphinate group. Compounds 1-14 were characterized by 1H, 13C, 11B, 31P NMR, IR, MS, EA, and MP. Compounds 5, 6, and 11-14 also were characterized by single-crystal X-ray diffraction.

Original languageEnglish
Pages (from-to)9213-9224
Number of pages12
JournalInorganic Chemistry
Volume45
Issue number23
DOIs
StatePublished - Nov 13 2006

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Inorganic Chemistry

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