Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...
Reexamination Certificate
2004-12-10
2009-12-15
Wilson, James O (Department: 1624)
Organic compounds -- part of the class 532-570 series
Organic compounds
Unsubstituted hydrocarbyl chain between the ring and the -c-...
Reexamination Certificate
active
07632943
ABSTRACT:
A novel reaction scheme is presented for making a 3,3,7,7-tetrakis(difluoramino)octahydro-1,5-diazocinium salt, such as HNFX, from a tetrahydro-1,5-diazocine-3,7(2H,6H)-dione that does not employ N-nitrolysis,—but that instead requires protolytic N-deprotection, or protolytic denosylation, (i.e., the nosyl N-protecting group is replaced with protons, forming the corresponding protonated amine or ammonium derivative). In summary, the present method subjects a suitably N-protected dione to difluoramination followed by protolytic N-deprotection by addition of a superacid and subsequent nitration utilizing an electrophilic nitrating agent to yield the diazocinium salt.
REFERENCES:
U.S. Appl. No. 11/010,058, filed Dec. 2004, Chapman et al.
Chapman et al. Difluoramination of heterocyclic Ketones: Control of Microbasicity, Journal of Organic Chemistry, 1998, 63, 1566-1570.
Chapman et al. Nitrolysis of Highly Deactivated Amide by Protonitronium Synthesis and Structure of HNFX, Journal of Organic Chemistry. 1999, 64, 960-965.
Chapman Robert D.
Groshens Thomas J.
Drazich Brian F.
Haley Charlene
Jarrell Noble
The United States of America as represented by the Secretary of
Wilson James O
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