Novel Synthesis of Cubane Precursor

Award Information
Agency: Department of Defense
Branch: Air Force
Contract: N/A
Agency Tracking Number: 20056
Amount: $375,000.00
Phase: Phase II
Program: SBIR
Solicitation Topic Code: N/A
Solicitation Number: N/A
Solicitation Year: N/A
Award Year: 1994
Award Start Date (Proposal Award Date): N/A
Award End Date (Contract End Date): N/A
Small Business Information
Chicago Technology Park, 2201, W Campbell Park Dr, Chicago, IL, 60612
HUBZone Owned: N
Woman Owned: N
Socially and Economically Disadvantaged: N
Principal Investigator
 Liang Guo
 (312) 421-1819
Business Contact
Phone: () -
Research Institution
Cubane C8H8 is potentially an extremely valuable fuel substitute for the kerosene-based rocket propellant RP-1. The classical Eaton synthesis to yield cubane 1,4-dicarboxylic acid in five steps involves a key photochemical reaction. The steps before and after the critical 2+2 cycloaddition are standardized and readily scalable. However, this steps alone prevents scale-up. We will develop a non-photochemical method for this step. We propose three chemical alternatives: a) radical cation 2+2 cycloaddition via a radical chain process, b) a cobalt catalyzed 2+2 cyclodimerization and c) a nucleophilic addition-cyclization route. Rapid analysis for the success in non-photochemical reaction of the chemical 2+2 is easily done because the properties of the product are already known. Therefore during the six month period of Phase I we will start a screening of many one-electron oxidants for radical cation formation (route a), exhaustively vary reaction parameters for the cobalt catalyzed cyclodimerization, (route b) and investigate a representative number of nucleophiles capable of triggering the intramolecular cyclization in route c.

* Information listed above is at the time of submission. *

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