US3941809A
Expired / Lapsed
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Technique for preparation of fulvalenes
Assignee: AT&T Inc
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Filing: 1975-01-20
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Granted: 1976-03-02
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Expires: 1995-01-20
Abstract
Abstract A technique for preparing a wide range of fulvalenes by a reductive procedure is described. The procedure involves reducing an organic halide to its corresponding partially hydrogenated derivative which is reacted with fluoboric acid to yield a fluoborate. Deprotonation of the fluoborate yields the desired compound. The described technique maximizes the yield and quality of fulvalenes produced and permits the preparation of thia, selena and tellura fulvalenes.
Inventors
- 👤 Martin Louis Kaplan
- 👤 Fred Wudl
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 21:11
CPC Classifications
C; C07; C07D; C07D339/00; C07D339/02; C07D339/06
Claims Analysis
Total Claims: 5
Claim 1
Independent Claim
119 words
Method for the preparation of a fulvalene which comprises the steps of a. reducing an organic halide of the general formula ##SPC6## with a reducing agent selected from the alkali and alkaline earth metal borohydrides at a temperature less than 15°C. wherein X is selected from the group consisting of sulfur, selenium and tellurium, Y is selected from the group consisting of sulfur and selenium, n is an integer from 0-4 and Z if a halogen atom, so resulting in the formation of the corresponding partially hydrogenated compound ##SPC7## b. reacting the partially hydrogenated derivative with fluorboric acid to yield the corresponding fluoborate derivative, and c. deprotonating the fluoborate derivative with an alkyl tertiary amine to yield the fulvalene.
Claim 2
Dependent Claim
119 words
Method for the preparation of a fulvalene which comprises the steps of a. reducing an organic halide of the general formula ##SPC6## with a reducing agent selected from the alkali and alkaline earth metal borohydrides at a temperature less than 15°C. wherein X is selected from the group consisting of sulfur, selenium and tellurium, Y is selected from the group consisting of sulfur and selenium, n is an integer from 0-4 and Z if a halogen atom, so resulting in the formation of the corresponding partially hydrogenated compound ##SPC7## b. reacting the partially hydrogenated derivative with fluorboric acid to yield the corresponding fluoborate derivative, and c. deprotonating the fluoborate derivative with an alkyl tertiary amine to yield the fulvalene.
Claim 3
Dependent Claim
32 words
Method in accordance with claim 1 wherein the alkyl tertiary amine is of the general formula [CH 3 (CH 2 ) n ] 3 N wherein n is an integer from 0-4.
Claim 4
Dependent Claim
11 words
Method in accordance with claim 1 wherein the fulvalene is 1,4,5,8-tetrahydro-1,4,5,8-tetrathiafulvalene.
Claim 5
Dependent Claim
41 words
Method in accordance with claim 3 wherein the fulvalene is prepared by reducing 2-thiomethyl-1,3-ditholium iodide with sodium borohydride to yield 2-S-methyl-1,3-dithiole, reacting the dithiole with fluoboric acid to yield 1,3-dithiolium fluoborate, and deprotonating the fluoborate with triethylamine to yield the fulvalene.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-03-02 | 1979-09-01 | 1980-03-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-03-02 | 1983-09-01 | 1984-03-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-03-02 | 1987-09-01 | 1988-03-02 | $7700.00 | Window Closed / Lapsed |