1.1- diacetoxy

Hexane 1,2-Diacetoxy-nonafluoro-1-phenylthio-1H,2H- E10b2, 192 (Ar —SO —CH2 —CHRF —OH + Ac20)... 

Octane 1,2-Diacetoxy-1-phenylthio-tridecafluoro-lII,2H- E10b2, 192 (ArSO-CII, -C HRF-OH + Ac,0)... 

Decane 1,2-Diacetoxy-heptadeca-fluoro-l-phenylthio-1 H.2H-EI0b2. 192... 

To a stirred solution of DIB (3.2 g, 10 mmol) in dichloromethane (40 ml) the silyl ether (1.7 g, 10 mmol) in dichloromethane (20 ml) was added at room temperature, under argon. After 6 h, the reaction mixture was concentrated and the residue extracted with pentane the extract was concentrated and then distilled to give 1-trimethylsilyloxy-2-acetoxy-cyclohexene (1.78 g, 78%), b.p. 55°C (0.2 mmHg). A by-product (7%) was 1,2-diacetoxy-l-trimethylsilyloxy-cyclohexane. 

Some mono- and di-substituted alkenes have been converted to 1,2-diacetoxy compounds by heating them in acetic acid solution with ammonium persulfate and a catalytic amount of iron(II) sulfate. Anti addition is observed with 1,2-disubstituted altenes with trisubstituted alkenes conqrlex mixtures are obtained. 

Butan 1,2-Diacetoxy-l-ethoxy-Vl/la, 1, 139f., 212, 214 Butandisaure 2-Ethyl-3-hydroxy- -diethylester E21a, 733 (2-H -v 2-C2H5)... 

The major product is cinnamyl acetate (2) a-phenylallyl acetate (3), 1,2-diacetoxy-.3-phenylpropane (4), and fran -propenylbenzene (5) are formed in trace amounts. A similar distribution of allylic acetates is obtained from the solvolysis of cinnamyl-mercuric acetate. C(,H5CH=CHCH2HgOAc, which presumably is the intermediate in the oxidation of allylbenzene. 

The mitosane A -oxide derivative (57) is similarly converted into the pyrroloindole derivative (58) in high yield upon reaction with acetic anhydride in chloroform (equation 17). The corresponding reaction of the 1,2-diacetoxy derivative (59) is more complex, however, as there is no directing functionality to orient the reaction (Scheme 11). One of the reaction products (62) is viewed as being formed via intermediates (60) and (61). If this mechanistic rationale is correct then the transformation of (59) to (62) represents a new manifestation of the Polonovski reaction. 

Preparation. Reppe et al. prepared this diene from cyclooctatetraene by the reactions formulated, but regarded it as 1,2-diacetoxy-A -cyclobutene. Criegee et al. established the true structure, and Hill and Carlson report a short preparative... 

Diacetoxy-l,2-d%cyan-cydobntan. Ihre nur langsame Bildung diirfte auf sterischer Hinderung des Ringschlusses berulien. 

Diacetoxy-l-alkoxy alkanes and 1,1,2-triacetoxy ethane64 are easily prepared by adding 1 mole of bromine to 1 mole of a vinyl ether or of vinyl acetate, respectively, in acetic anhydride containing 2 moles of anhydrous sodium acetate. This triacetate can be converted, without isolation, into DL-serine by a modified Strecker synthesis.65... 

A potentially quite useful synthetic method was recently reported by Sawyer and Kuivila 240-242), who treated diorganotin dihydrides with carboxylic acids to obtain functionally substituted ditin compounds. Thus, the reaction of dibutyltin dihydride with acetic acid leads to 1,2-diacetoxy-tetra-n-butylditin in 65% yield. 

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