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Use of Sodium Benzyl Selenodithicocarbonate for the Preparation of Selenocarbonyl 1 3 Dithiole and 1 3 Diselenole Derivatives

IP.com Disclosure Number: IPCOM000084546D
Original Publication Date: 1975-Nov-01
Included in the Prior Art Database: 2005-Mar-02
Document File: 2 page(s) / 38K

Publishing Venue

IBM

Related People

Engler, EM: AUTHOR [+2]

Abstract

Charge-transfer salts of tetrathiafulvalene, its selenium analog and its substituted derivatives (1) are among the most electrically conducting organic solids presently known. The key synthetic step in preparing these tetrathiafulvalene donors involves the coupling of compounds such as 2. (Image Omitted)

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Use of Sodium Benzyl Selenodithicocarbonate for the Preparation of Selenocarbonyl 1 3 Dithiole and 1 3 Diselenole Derivatives

Charge-transfer salts of tetrathiafulvalene, its selenium analog and its substituted derivatives (1) are among the most electrically conducting organic solids presently known. The key synthetic step in preparing these tetrathiafulvalene donors involves the coupling of compounds such as 2.

(Image Omitted)

While a variety of synthetic procedures are aVailable for coupling compound 2; most of these methods depend very much on the nature of the heteroatom (X and Y) and the R substituent.

The most general coupling method appears to be the use of phosphorous bases to couple 2. In fact, this procedure is the only means capable of preparing selenium TTF derivatives (X = Se). For unsubstituted systems (R = H) when Y = S, this coupling reaction does not work.

Only when Y = Se does the reaction work well. The reason for this is undoubtedly due to the weaker C=Se bond which can be more easily broken, under milder reaction conditions. This quality of the C=Se, also typically leads to better yields and more easily isolated products for the substituted derivatives of TTF.

Unfortunately, most syntheses of 2 lead to a thiocarbonyl and good synthetic methods for converting C=S to C=Se are lacking. A new synthetic procedure for preparing selenocarbonyl derivatives of 2 starting from elemental selenium is hereafter described. This method uses the new reagent:...