Accession Number:

ADA243380

Title:

Nitration and Nitrocompounds

Descriptive Note:

Final rept. 1988-1991

Corporate Author:

UNIVERSITY OF SOUTHERN CALIFORNIA LOS ANGELES

Personal Author(s):

Report Date:

1991-01-01

Pagination or Media Count:

9.0

Abstract:

In the course of studying new superacid system in nitration we evaluated the nitric-tetratriflatoboric acid system HNO3-HBO3SCF34 for its nitrating ability of aromatics. Tetratriflatoboric acid, HBO3SCF34 was conveniently prepared in situ from triflic acid excess and boron trichloride and could be used without any workup. Nitration of benzene, toluene, fluorobenzene, chlorobenzene, anisole and naphthalene was studied with HNO3-HBO3SCF34 in methylene chloride solution at -30 deg C and at room temperature. the new superacidic nitration of toluene gave very low 1 meta nitration both at - 30 deg C and at room temperature. At the same time the ortholpara isomer ratio is also lower than in most studied nitronium ion nitrations, indicating ion pairing or association with bulky tetratriflatoborate anion. Similarly high regiopositional selectivity was found in nitration of the other aromatics.

Descriptors:

• *IONS
• ROOM TEMPERATURE
• SOLUTIONS(GENERAL)
• CHLORIDES
• AROMATIC COMPOUNDS
• CHLOROBENZENE
• NITROGEN OXIDES
• BORON
• INDICATORS
• NITRATION
• NAPHTHALENES
• ANISOLE
• BENZENE
• METHYLENES

Subject Categories:

• Organic Chemistry

Distribution Statement:

APPROVED FOR PUBLIC RELEASE