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

Glen A. Russell, Ching-Fa Yao

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Abstract

Photolysis of t‐BuHgCl/KI with PhC(R2)C(R1)NO2 forms PhC(R2)C(R1)Bu‐t when R1 = R2 = H or in low yield when R1 = 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(R1)N(OBu‐t)OHgX+, PhC(R2)C(R1)NO and PhC(R2)C(R1)N(OBu‐t)HgX to form a variety of novel products including the dimeric bisnitronic esters (6) with R1 = Me or Ph and R2 = H; PhCH(R2)C(R1) = NOBu‐t with R1 = Me or Ph and R2 = H or R1 = H and R2 = Ph; PhC(R2)(OBu‐t)C(R1)NOH with R1 = H or Me and R2 = Ph; and 3‐phenyl‐2‐R1‐indoles with R1 = H, Me, Ph, PhS or t‐BuS and R2 = Ph. Nitrosoaromatics react with t‐BuHgX in the dark to form ArN(OBu‐t)(OBu‐t)HgX+ which condenses with ArNO to form the azoxy compound. tert‐Butyl radicals will add to RNO2 [R = Ph, Ph2CCH, Ph2CC(Ph)] in the presence of t‐BuHgI2 to form products derived from RN(OBu‐t)OHgI+.

Original languageEnglish
Pages (from-to)209-218
Number of pages10
JournalHeteroatom Chemistry
Volume3
Issue number3
DOIs
Publication statusPublished - 1992 Jan 1

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Reactions of β‐nitrostyrenes with tert‐butylmercury halides in the presence of lodide lon. / Russell, Glen A.; Yao, Ching-Fa.

In: Heteroatom Chemistry, Vol. 3, No. 3, 01.01.1992, p. 209-218.

Research output: Contribution to journalArticle

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abstract = "Photolysis of t‐BuHgCl/KI with PhC(R2)C(R1)NO2 forms PhC(R2)C(R1)Bu‐t when R1 = R2 = H or in low yield when R1 = 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(R1)N(OBu‐t)O−HgX+, PhC(R2)C(R1)NO and PhC(R2)C(R1)N(OBu‐t)HgX to form a variety of novel products including the dimeric bisnitronic esters (6) with R1 = Me or Ph and R2 = H; PhCH(R2)C(R1) = NOBu‐t with R1 = Me or Ph and R2 = H or R1 = H and R2 = Ph; PhC(R2)(OBu‐t)C(R1)NOH with R1 = H or Me and R2 = Ph; and 3‐phenyl‐2‐R1‐indoles with R1 = H, Me, Ph, PhS or t‐BuS and R2 = Ph. Nitrosoaromatics react with t‐BuHgX in the dark to form ArN(OBu‐t)(OBu‐t)HgX+ which condenses with ArNO to form the azoxy compound. tert‐Butyl radicals will add to RNO2 [R = Ph, Ph2CCH, Ph2CC(Ph)] in the presence of t‐BuHgI2− to form products derived from RN(OBu‐t)O−HgI+.",
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AB - Photolysis of t‐BuHgCl/KI with PhC(R2)C(R1)NO2 forms PhC(R2)C(R1)Bu‐t when R1 = R2 = H or in low yield when R1 = 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(R1)N(OBu‐t)O−HgX+, PhC(R2)C(R1)NO and PhC(R2)C(R1)N(OBu‐t)HgX to form a variety of novel products including the dimeric bisnitronic esters (6) with R1 = Me or Ph and R2 = H; PhCH(R2)C(R1) = NOBu‐t with R1 = Me or Ph and R2 = H or R1 = H and R2 = Ph; PhC(R2)(OBu‐t)C(R1)NOH with R1 = H or Me and R2 = Ph; and 3‐phenyl‐2‐R1‐indoles with R1 = H, Me, Ph, PhS or t‐BuS and R2 = Ph. Nitrosoaromatics react with t‐BuHgX in the dark to form ArN(OBu‐t)(OBu‐t)HgX+ which condenses with ArNO to form the azoxy compound. tert‐Butyl radicals will add to RNO2 [R = Ph, Ph2CCH, Ph2CC(Ph)] in the presence of t‐BuHgI2− to form products derived from RN(OBu‐t)O−HgI+.

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