Synthesis of S-alkyl and S-acyl derivatives of Mercaptoundecahydrododecaborate, a possible boron carrier for neutron capture therapy

Journal Article · Wed May 26 04:00:00 EDT 1993 · Inorganic Chemistry; (United States)

DOI:https://doi.org/10.1021/ic00063a014· OSTI ID:5784391

Gabel, D; Moller, D; Harfst, S; Roesler, J; Ketz, H ^[1]

---

1. Univ. of Bremen (Germany)

The synthesis of S-alkylated and S-acylated derivatives of mercaptoundecahydrododecaborate (B[sub 12]H[sub 11]SH[sup 2][sup [minus]]) (1) is described. Under conventional alkylation conditions, 1 reacts with primary alkyl halides to form S,S-bis-substituted sulfonium salts. With secondary halides, monoalkylation to thioethers is observed. The sulfonium salts act only as poor alkylating agents. The cyanoethyl-substituted sulfonium salt 3 was found to lose one substituent upon treatment with tetramethylammonium hydroxide, to yield the thioether 8. Unsymmetrically substituted sulfonium salts were obtained through realkylation. Selective removal of the remaining cyanoethyl group yielded thioethers. Reaction of 1 with acid halides resulted in thioesters, which showed surprising stability toward hydrolysis.

• OSTI ID: 5784391
• Journal Information: Inorganic Chemistry; (United States), Journal Name: Inorganic Chemistry; (United States) Vol. 32:11; ISSN 0020-1669; ISSN INOCAJ
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
550603 -- Medicine-- External Radiation in Therapy-- (1980-)
62 RADIOLOGY AND NUCLEAR MEDICINE
ACID HALIDES
BORANES
BORON COMPOUNDS
CHALCOGENIDES
CHEMICAL PREPARATION
CHEMICAL REACTIONS
HYDRIDES
HYDROGEN COMPOUNDS
MEDICINE
NEUTRON CAPTURE THERAPY
NEUTRON THERAPY
NUCLEAR MEDICINE
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
RADIOLOGY
RADIOTHERAPY
SULFIDES
SULFUR COMPOUNDS
SYNTHESIS
THERAPY