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Reactions of β-nitrostyrenes with tert-butylmercury halides in the presence of lodide lon

✍ Scribed by Glen A. Russell; Ching-Fa Yao

Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
888 KB
Volume
3
Category
Article
ISSN
1042-7163

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✦ Synopsis

Photolysis of t-BuHgCUIU with PhC(R2) = C(R1)N02 foriiis PhC(R2=C(R')Bu-t when R' = R2 = H or in low yield when R' = H, R2 = Ph. When R1 # H, or when R2 = Ph, reactions with t-BuHgI/KI/hv proceed mainly via PhC(R2) =C(R1)NO2*-, PhC(R2) = C(R')N(OBu-t)O-HgX + , PhC(R2) =C(R')N=O and PhC(R2) =C(R')N(OBu-t)HgX to fonii a variety of novel products including the dimeric bisnitronic esters (6) with R' = Me or Ph and R2 = H; PhCH(R2)C(R1) = NOBu-t with R' = Me or Ph and R2 = H or R' = H and R2 = Ph; PhC(R2)(OBu-t)C(R1)=NOH with R' = H or Me and R2 = Ph; and 3-pheiiyl-2-R1-indoles with R' = H, Me, Ph, PhS or t-Bus and R2 = Ph-Nitrosoaroillatics react with t-BuHgX in the dark to fonii ArN(0Bu-t) (OBu-t) HgX which condenses with ArNO to fonii the azoxy coinpound. tert-Butyl radicals will add to RN02 [R = Ph, Ph2C=CH, Ph2C=C(Ph)] in the presence of t-BuHg12to fonn products derived from RN(0Bu-t)O-HgI ?

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Cyclizations are observed in the homolytic reactions of t-BuHgI with CH 2 CHCH 2 YCH 2 CN [Y = CH 2 , O, CMe 2 , C(CO 2 Et) 2 , NCH 2 CN] and CH 2 CHCH 2 CH 2 YCH 2 CN [Y = CH 2 , O, C(CO 2 Et) 2 ] in Me 2 SO in the presence of hydriodic acid. Only with Y = C(CO 2 Et) 2 does the adduct radical, t-Bu

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