METHANESULFONYL CYANIDE

Contrary to the findings of Cox and Ghosh, methanesulfonyl cyanide may be distilled without decomposition. Samples of benzene-, p-methoxybenzene-, and p-chlorobenzenesulfonyl cyanides were kept for over a year without loss in purity. 

The procedure given above for the preparation of methanesulfonyl cyanide essentially is a combination of the sulfite reduction of a sulfonyl... 

METHANESULFONYL CYANIDE, 57, 88 Methane, triphenyl-, 55, 11 Methanol, (4-methylphenylsulfonyl) esters, perchlorate, 57, 100... 

Lonza operate a continuous process for the production of Vince lactam [23]. This is a component of the anti-HIV reverse transcriptase inhibitors, abacavir and carbovir (Scheme 11.11) [24]. Methanesulfonyl cyanide is generated in situ and reacted catalyhcally (10mol%) with cyclopentadiene in a flow process. The resulting Diels-Alder adduct is hydrolyzed to produce Vince lactam. The methanesulflnic... 

Mercaptobenzimidazole, 30, 56 2-Mercaptobenzoxazole, 30, 57 Mercuric cyanide, 32, 31 Methallyl chloride, 32, 90 Methanephosphoric acid, diisopropyl ESTER, 31, 33 Methanesulfonic acid, 30, 58 Methanesulfonyl chloride, 30, 58 Methanol, 30, 31 32, 79 Methone, 31, 40... 

Boger and Corbett have also recently described a convenient modification of the original Hudson methodology [20]. Their procedure is based upon the known [21] propensity of methanesulfonyl- and toluenesulfonyl cyanide to rearrange to the corresponding sulfinyl cyanate (cf. 8, Scheme 4). Thus, treatment of an oxime with commercially available tosyl cyanide (7) generates 8 in situ, which leads to the O-sulfinylated oxime 9 and then to the N-tosyl imine. This methodology avoids the use of reactive, often unstable sulfinyl chlorides. 

An unusual stereospecific ring contraction has been observed upon attempted substitution of 4-0-activated pentono-1,5-lactams with cyanide. The reaction of 4-0-methanesulfonyl-2,3-0-isopropylidene-D-ribo- or -D-lyxo-1,5-lactams with tetrabutylammonium cyanide gave 4-amino-5-C-cyano-4,5-dideoxy-2,3-0-iso-propylidene-L-lyxo- or -L-ribo-l,4-lactams respectively (Scheme 16), instead of the expected products of simple Sn displacement of mesylate by cyanide. Reduc-... 

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