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1 AD- A \\IIl\\l/\\ll\\\I/ (\I\\\Il\\\lI\/I/III OFFICE OF NAVAL RESEARCH Contract N K-0772 Work Unit No TECHNICAL REPORT NO. 139 A Ferracarborane Analogue to [Fp]-. Synthesis and Reactions of [closo-3,3-(c0)2-3,1,2-fec2b 9 H 11]2- by Sharon S. Lee, Carolyn Knobler, and M. Frederick Hawthorne* Prepared for Publication in Organonetallics 4 University of California at Los Angeles Department of Chemistry and Biochemistry Los Angeles, California 90024,. April, 1991 Reproduction in whole or in part is permitted for any purpose of the United States Government _ J This document has been approved for public release and sale: its distribution is unlimited
2 Unclassified SECURITY CLASSIFICATION OF THI5 PAG REPORT DOCUMENTATION PAGE is. REPORT SECURITY CLASSIFICATION 1b. RESTRICTIVE MARKINGS UNCLASSIFIED 2s. SECURITY CLASSIFICATION AUTHORITY 3. DISTRIBUTION /AVAILABILITY OF REPORT 2b. DECLASSIFICATION/IDOWNGRADING SCHEDULE Distribution list enclosed 4. PERFORMING ORGANIZATION REPORT NUMBER(S) S. MONITORING ORGANIZATION REPORT NUMBER(S) 139 6a. NAME OF PERFORMING ORGANIZATION 6.OFFICE SYMBOL 7a NAME OF MONITORING ORGANIZATION UCLA 1b(if applicable) Ofc fnvlrsac Dept. of Chem. & Biochen. I fieo avlrsac 6c. ADDRESS (City, State, and ZIP Code) 7b. ADDRESS (City, State, and ZIP Code) 6115 Young Hall Department of the Navy 405 Hilgard Avenue Los Angeles, CA 90024s Arlington, VA Sa. NAME OF FUNDING /SPONSORING 8 b OFFICE SYMBOL 9. PROCUREMENT INSTRUMENT IDENTIFICATION NUMBER Office of Naval Research Sc. ADDRESS (City, State, and ZIP Code) Ifapcbe 11. TITLE (include Security Ciassification) A Ferracarborane Analo ue to [FpJ-. 2 Synthesis anc d eacions of [closo-3,3- (C0) 2-3,, 2-FeC 2 B 9 Hll 1 10 SOURCE OF FUNDING NUMBERS PROGRAM IPROJECT ITASK IWORK UNIT ELEMENT NO INO. INO IACCES NO 12 PERSONAL AUTHOR(S) Sharon S. Lee, Carolyn Knobler, and M. Frederick Hawthorne _ PG ON 13a TYPE OF REPORT 13b TIME COVERED 114 DATE OF FI9T(Year Month, Day) 15PG ON Technical Repor FROM TO 11249i I 16 SUPPLEMENTARY NOTATION To be published in OrganometalliQs_ 17 COSATI CODES IB SUBJECT TERMS (Continue on reverse if necessary and identify by block number) FIELD GROUP SUB-GROUP Metallacarborane, dicarbollide, iron, iron carbonyl 19 ABSTRACT (Continue on reverse if necessary and identify by block number) Reduction of Icloso-3,3,3-(CO)a-3,1,2-FeCBHu (1) with 2 equiv of sodium naphthalide affords the high-yield synthesis of a formal iron(o) ferracarborane dianion [cioso-3,3-(co)2-3,1,2-fec*bs, 1 1J- (3), as monitored by 11 B NMR spectroscopy. Complex 3 serves as a nucleophile in a variety of alkylation, acylation, and metaistion reactions to yield ferracarborane anions of the type [closo-3,3-(co)-3-l-3,l,2-fece,bn (4, L -OH 3 ; 5, L -CH 2 CG, 5 ; 6, L -COCH 3 ; 7, L -SnCGHd. The molecular structure of (N(C2,]l[71 has been determined by X-ray diffraction techniques. Compound 7 crystallized in the triclinic space group P! with a = (1) A, b = (1) A. c (1) A, a = (3)0, (3)*, -V (2)", V = 1785 A 3, and Z = I. n situ reations of 3 vith allyl and methylallyl chloride followed by subsequent loss of CO induced by ultraviolet radiation, resulted in the isolation of the corresponding 9?-aIl~yl derivatives, Iclso-3-CO-3-(,,?-CH 2 CRCH)-3,l,2-FeClsHn1l (8, R -H; 9, R = H). The structure of 8 as the PPN* salt was also elucidated by single-crystal X-ray diffraction and found to crystallize in the monoclinic spac group P2 1 /m with a = (7) A, b = (2) A, c = (2) A, oi (3)0, V A 3, and Z -4 (two crystallographically different half-anions and one cation in the asymmetric unit). Migratory 20 DISTRIBUTION /AVAILABILITY OF ABSTRACT 21. ABSTRACT SECURITY CLASSIFICATION [!UNCLASSIFIEDIUNLIMITED 0 SAME AS RPT 0 DTIC USERS Unclassified 22& NAME OF RESPONSIBLE INDIVIDUAL 22b TELEPHONE (include Area Code) 22c OFF ICE SYMBOL M. F. Hawthorne (213) I OD FORM 1473,84 MAR 83 APR ed-t-ot may be used until exhausted. All othef editions are obsolete. SECURITY CLASSIFICATION OF THIS PAGE
3 19. Abstract (cont.) insertion of alkyls was demonstrated in the preparation of (closo-3-co4-(ch -P(CH)r3,1.-FeC B. Ir (10) by heating 4 and excess P(CH3)3 in THF for 7 days at the reflux temperatu.a single-crystal X-ray diffraction study of IPPN] 110] is reported. Complex 10 crystallized in the triclinic space group P with a (4) A, b = (6) A, c (7) A, a (8)*, (8)0, (9)0, V 2351 A s, and Z -2. The closo 12-vertex icosahedral geometry composed of a polyhedral FeCBs-, framework and pseudooctabedral coordination exhibited by the iron atom are common structural features displayed by all three of the ferracarboranes that were characterized crystallographically.
4 A Ferracarborane Analogue to [Fp]-. Synthesis and Reactions of [closo-3,3-(co) 2-3,1,2-FeC 2B9Hl 1 ] 2- Sharon S. Lee, Carolyn B. Knobler, and M. Frederick Hawthorne Depmrdent of Chemistry and B4ochemstry, Unvrsfty of Cafoids, Los Angeles, Los Angeles. Caifornia Received July 6, 1990 Reduction of jcloso-3,3,3-(co) 3-3,1,2-FeCBgllI (1) with 2 equiv of sodium naphthalide affords the high-yield synthesis of a formal iron(0) ferracarborane dianion [closo-3,3-(co) 2-3,1,2-FeC 2 BHll] - (3), as monitored by 'ib NMR spectroscopy. Complex 3 serves as a nucleophile in a variety of alkylation, acylation, and metalation reactions to yield ferracarborane anions of the type [closo-3,3-(co) 2-3-L-3,1,2-FeC 2 BH 11 ] (4, L = CH 3 ; 5, L = CH 2 C 6 H 6 ; 6, L = COCH 3 ; 7, L = SnC 6 Hs). The molecular structure of [N(C 2 H 6 ) 4 ][7] has been determined by X-ray diffraction techniques. Compound 7 crystallized in the triclinic space group P! with a = (1) A, b = (1) A, c = (1) A, a = (3)0,, = (3), -y = (2), V = 1785 A 3, and Z = 2. In situ reactions of 3 with allyl and methylallyl chloride followed by subsequent loss of CO induced by ultraviolet radiation, resulted in the isolation of the corresponding e-allyl derivatives, - [closo-3-co-3-(,s-ch 2 CRCH)-3,1,2-FeC2BHul] (8, R = H; 9, R = CH 3 ). The structure of 8 as the PPN + salt was also elucidated by single-crystal X-ray diffraction and found to crystallize in the monoclinic space group P2 1 /m with a = (7) A, b = (2) A, c = (2) A, # = (3)0, V = 4225 A 3, and Z = 4 (two crystallographically different half-anions and one cation in the asymmetric unit). Migratory insertion of alkyls was demonstrated in the preparation of [c/oso-3-co-3-coch3-3-p(chshr3,1,2-fec 2 BJi]- (10) by heating 4 and excess P(CH 3 ) 3 in THF for 7 days at the reflux temperature. A single-crystal X-ray diffraction study of [PPN][10] is reported. Complex 10 crystallized in the triclinic space group P1 with a = (4) A, b = (6) A, c = (7) A, a = (8)0, f = (8), -y = (9)0, V = 2351 A 3, and Z = 2. The closo 12-vertex icosahedral geometry composed of a polyhedral FeC 2 BO-d 6 framework and pseudooctahedral coordination exhibited by the iron atom are common structural features displayed by all three of the ferracarboranes that were characterized crystallographically.
5 dl/1113/86/2 TECHNICAL REPORT DISTRIBUTION LIST, GEN No. Copies No. Copies Office of Naval Research Attn: Code Dr. David Young Code N. Quincy Street NORDA Arlington, Virginia NSTL, Mississippi Dr. Bernard Douda Naval Weapons Support Center 1 Naval Weapons Center Attn: Dr. Ron Atkins Code 50C Chemistry Division Crane, Indiana China Lake, California Scientific Advisor Naval Civil Engineering Laboratory 1 Commandant of the Marine Corps Attn: Dr. R. W. Drisko, Code L52 Code RD-I Port Hueneme, California Washington, D.C U.S. Army Research Office Defense Technical Information Center 12 Attn: CRD-AA-IP Building 5, Cameron Station high P.O. Box Alexandria, Virginia quality Research Triangle Park, NC Mr. John Boyle 1 DTNSRDC 1 Materials Branch Attn: Dr. H. Singerman Naval Ship Engineering Center Applied Chemistry Division Philadelphia, Pennsylvania Annapolis, Maryland Dr. William Tolles I Naval Ocean Systems Center Attn: Dr. S. Yamamoto 1 Superintendent Marine Sciences Division Chemistry Division, Code 6100 San Diego, California Naval Research Laboratory Washington, D.C
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