e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Synthesis and Chemistry of 1H-Cyclobuta [de] naphthalenes, 1-Alkylidene-1H-cyclobuta [de] naphthalenes, and 1H-Cyclobuta [de] naphthalen-1-one

PJ Card, FE Friedli, H Shechter

Index: Card,P.J.; Friedli,F.E.; Shechter,H. Journal of the American Chemical Society, 1983 , vol. 105, p. 6104

Full Text: HTML

Citation Number: 10

Abstract

Abstract: Grignard and lithium reagents from 1-bromo-lH-cyclobuta [de] naphthalene (la) are converted by protonic acids, trimethylsilyl chloride, methyl iodide, carbon dioxide, acetyl chloride, and ethylene oxide to the corresponding lH-cyclobuta [de] naphthalene derivatives. Further, displacements of la by various nucleophiles (aluminohydrides, iodide, chloride, cyanide, azide, methoxide and thiophenoxide, triphenylphosphine, silver nitrate, acetate, ...

(1H-cyclobuta[de]naphthalen-1-yl)lithium Structure

(1H-cyclobuta[d...

~95%

1-Methylnaphthalene Structure

1-Methylnaphthalene

1-(Diphenylmethylene)-1H-cyclobuta(de)naphthalene Structure

1-(Diphenylmeth...

~95%

1,2-diphenylacenaphthlene Structure

1,2-diphenylace...

1-bromo-1H-cyclobuta[de]naphthalene Structure

1-bromo-1H-cycl...

~%

1,2-diphenylacenaphthlene Structure

1,2-diphenylace...

1H-Cyclobuta[de]naphthalene Structure

1H-Cyclobuta[de...

~%

1,2-diphenylacenaphthlene Structure

1,2-diphenylace...

(1H-cyclobuta[de]naphthalen-1-yl)lithium Structure

(1H-cyclobuta[d...

~%

1,2-diphenylacenaphthlene Structure

1,2-diphenylace...

1-(triphenylphosphino)-1H-cyclobuta(de)naphthalene bromide Structure

1-(triphenylpho...

~%

1,2-diphenylacenaphthlene Structure

1,2-diphenylace...

(1H-cyclobuta[de]naphthalen-1-yl)magnesium bromide Structure

(1H-cyclobuta[d...

~%

1,2-diphenylacenaphthlene Structure

1,2-diphenylace...

1-bromo-1H-cyclobuta[de]naphthalene Structure

1-bromo-1H-cycl...

~%

1-prop-1-ynylnaphthalene Structure

1-prop-1-ynylna...

1H-Cyclobuta[de]naphthalene Structure

1H-Cyclobuta[de...

~%

1-prop-1-ynylnaphthalene Structure

1-prop-1-ynylna...

(1H-cyclobuta[de]naphthalen-1-yl)lithium Structure

(1H-cyclobuta[d...

~%

1-prop-1-ynylnaphthalene Structure

1-prop-1-ynylna...

(1H-cyclobuta[de]naphthalen-1-yl)magnesium bromide Structure

(1H-cyclobuta[d...

~%

1-prop-1-ynylnaphthalene Structure

1-prop-1-ynylna...

1-ethylidene-1H-cyclobuta(de)naphthalene Structure

1-ethylidene-1H...

~44%

1-prop-1-ynylnaphthalene Structure

1-prop-1-ynylna...

1-acetyl-1H-cyclobuta(de)naphthalene Structure

1-acetyl-1H-cyc...

~%

1-prop-1-ynylnaphthalene Structure

1-prop-1-ynylna...

1-cyano-1H-cyclobuta(de)naphthalene Structure

1-cyano-1H-cycl...

~%

1-prop-1-ynylnaphthalene Structure

1-prop-1-ynylna...

3'-methylspiro(1H-cyclobuta(de)naphthalene-1,2'-oxirane) Structure

3'-methylspiro(...

~%

1-prop-1-ynylnaphthalene Structure

1-prop-1-ynylna...

1-acetyl-1H-cyclobuta(de)naphthalene p-tosylhydrazone Structure

1-acetyl-1H-cyc...

~%

1-prop-1-ynylnaphthalene Structure

1-prop-1-ynylna...

1-(triphenylphosphino)-1H-cyclobuta(de)naphthalene bromide Structure

1-(triphenylpho...

~%

1-prop-1-ynylnaphthalene Structure

1-prop-1-ynylna...

1H-cyclobuta(de)naphthalen-1-one Structure

1H-cyclobuta(de...

~90%

naphthoic acid Structure

1H-cyclobuta(de)naphthalen-1-one Structure

1H-cyclobuta(de...

Structure

~81%

N-phenylnaphthalene-1-carboxamide Structure

N-phenylnaphtha...

1-bromo-1H-cyclobuta[de]naphthalene Structure

1-bromo-1H-cycl...

~%

N-phenylnaphthalene-1-carboxamide Structure

N-phenylnaphtha...

1H-Cyclobuta[de]naphthalene Structure

1H-Cyclobuta[de...

~%

N-phenylnaphthalene-1-carboxamide Structure

N-phenylnaphtha...

(1H-cyclobuta[de]naphthalen-1-yl)lithium Structure

(1H-cyclobuta[d...

~%

N-phenylnaphthalene-1-carboxamide Structure

N-phenylnaphtha...

(1H-cyclobuta[de]naphthalen-1-yl)magnesium bromide Structure

(1H-cyclobuta[d...

~%

N-phenylnaphthalene-1-carboxamide Structure

N-phenylnaphtha...

1-(thiophenoxy)-1H-cyclobuta(de)naphthalene Structure

1-(thiophenoxy)...

~%

N-phenylnaphthalene-1-carboxamide Structure

N-phenylnaphtha...

1-chloro-1-(thiophenoxy)-1H-cyclobuta(de)naphthalene Structure

1-chloro-1-(thi...

~%

N-phenylnaphthalene-1-carboxamide Structure

N-phenylnaphtha...

1-(triphenylphosphino)-1H-cyclobuta(de)naphthalene bromide Structure

1-(triphenylpho...

~%

N-phenylnaphthalene-1-carboxamide Structure

N-phenylnaphtha...

1-(Trimethylsilyl)-1H-cyclobuta(de)naphthalene Structure

1-(Trimethylsil...

~82%

trimethyl(naphthalen-1-ylmethyl)silane Structure

trimethyl(napht...

1-methyl-1H-cyclobuta(de)naphthalene Structure

1-methyl-1H-cyc...

~80%

1-Vinylnaphthalene Structure

1-Vinylnaphthalene

1-bromo-1H-cyclobuta[de]naphthalene Structure

1-bromo-1H-cycl...

~%

Methanediol,1-(1-naphthalenyl)-, 1,1-diacetate Structure

Methanediol,1-(...

1-methylene-1H-cyclobuta(de)naphthalene Structure

1-methylene-1H-...

~%

1-Ethynylnaphthalene Structure

1-Ethynylnaphthalene

1-bromo-1H-cyclobuta[de]naphthalene Structure

1-bromo-1H-cycl...

~%

1-Ethynylnaphthalene Structure

1-Ethynylnaphthalene

1H-Cyclobuta[de]naphthalene Structure

1H-Cyclobuta[de...

~%

1-Ethynylnaphthalene Structure

1-Ethynylnaphthalene

(1H-cyclobuta[de]naphthalen-1-yl)lithium Structure

(1H-cyclobuta[d...

~%

1-Ethynylnaphthalene Structure

1-Ethynylnaphthalene

(1H-cyclobuta[de]naphthalen-1-yl)magnesium bromide Structure

(1H-cyclobuta[d...

~%

1-Ethynylnaphthalene Structure

1-Ethynylnaphthalene

1-(triphenylphosphino)-1H-cyclobuta(de)naphthalene bromide Structure

1-(triphenylpho...

~%

1-Ethynylnaphthalene Structure

1-Ethynylnaphthalene

1H-Cyclobuta[de]naphthalene Structure

1H-Cyclobuta[de...

~63%

Methanediol,1-(1-naphthalenyl)-, 1,1-diacetate Structure

Methanediol,1-(...

naphthal Structure

(1H-cyclobuta[de]naphthalen-1-yl)magnesium bromide Structure

(1H-cyclobuta[d...

~%

Methanediol,1-(1-naphthalenyl)-, 1,1-diacetate Structure

Methanediol,1-(...

1H-Cyclobuta[de]naphthalene Structure

1H-Cyclobuta[de...

Silver acetate Structure

~63%

Methanediol,1-(1-naphthalenyl)-, 1,1-diacetate Structure

Methanediol,1-(...

naphthal Structure

(1H-cyclobuta[de]naphthalen-1-yl)lithium Structure

(1H-cyclobuta[d...

~%

Methanediol,1-(1-naphthalenyl)-, 1,1-diacetate Structure

Methanediol,1-(...

1-acetoxy-1H-cyclobuta(de)naphthalene Structure

1-acetoxy-1H-cy...

~97%

1-Naphthylmethanol Structure

1-Naphthylmethanol

1-bromo-1H-cyclobuta[de]naphthalene Structure

1-bromo-1H-cycl...

~%

1-Naphthylmethanol Structure

1-Naphthylmethanol

1H-Cyclobuta[de]naphthalene Structure

1H-Cyclobuta[de...

~%

1-Naphthylmethanol Structure

1-Naphthylmethanol

(1H-cyclobuta[de]naphthalen-1-yl)lithium Structure

(1H-cyclobuta[d...

~%

1-Naphthylmethanol Structure

1-Naphthylmethanol

(1H-cyclobuta[de]naphthalen-1-yl)magnesium bromide Structure

(1H-cyclobuta[d...

~%

1-Naphthylmethanol Structure

1-Naphthylmethanol

1-acetoxy-1H-cyclobuta(de)naphthalene Structure

1-acetoxy-1H-cy...

~69%

naphthal Structure

1-bromo-1H-cyclobuta[de]naphthalene Structure

1-bromo-1H-cycl...

~60%

naphthal Structure

1-bromo-1H-cyclobuta[de]naphthalene Structure

1-bromo-1H-cycl...

Sodium Methylate Structure

Sodium Methylate

~0%

1-(dimethoxymethyl)naphthalene Structure

1-(dimethoxymet...

naphthal Structure

Detail

1-bromo-1H-cyclobuta[de]naphthalene Structure

1-bromo-1H-cycl...

~%

1-Isobutylnaphthalene Structure

1-Isobutylnapht...

1H-Cyclobuta[de]naphthalene Structure

1H-Cyclobuta[de...

~%

1-Isobutylnaphthalene Structure

1-Isobutylnapht...

1-(triphenylphosphino)-1H-cyclobuta(de)naphthalene bromide Structure

1-(triphenylpho...

~%

1-Isobutylnaphthalene Structure

1-Isobutylnapht...

(1H-cyclobuta[de]naphthalen-1-yl)magnesium bromide Structure

(1H-cyclobuta[d...

~%

1-Isobutylnaphthalene Structure

1-Isobutylnapht...

3'-methylspiro(1H-cyclobuta(de)naphthalene-1,2'-oxirane) Structure

3'-methylspiro(...

~90%

2-methyl-2H-acenaphthylen-1-one Structure

2-methyl-2H-ace...

1-bromo-1H-cyclobuta[de]naphthalene Structure

1-bromo-1H-cycl...

~%

2-methyl-2H-acenaphthylen-1-one Structure

2-methyl-2H-ace...

1H-Cyclobuta[de]naphthalene Structure

1H-Cyclobuta[de...

~%

2-methyl-2H-acenaphthylen-1-one Structure

2-methyl-2H-ace...

(1H-cyclobuta[de]naphthalen-1-yl)lithium Structure

(1H-cyclobuta[d...

~%

2-methyl-2H-acenaphthylen-1-one Structure

2-methyl-2H-ace...

(1H-cyclobuta[de]naphthalen-1-yl)magnesium bromide Structure

(1H-cyclobuta[d...

~%

2-methyl-2H-acenaphthylen-1-one Structure

2-methyl-2H-ace...

1-ethylidene-1H-cyclobuta(de)naphthalene Structure

1-ethylidene-1H...

~%

2-methyl-2H-acenaphthylen-1-one Structure

2-methyl-2H-ace...

1-acetyl-1H-cyclobuta(de)naphthalene Structure

1-acetyl-1H-cyc...

~%

2-methyl-2H-acenaphthylen-1-one Structure

2-methyl-2H-ace...

1-cyano-1H-cyclobuta(de)naphthalene Structure

1-cyano-1H-cycl...

~%

2-methyl-2H-acenaphthylen-1-one Structure

2-methyl-2H-ace...

1-acetyl-1H-cyclobuta(de)naphthalene p-tosylhydrazone Structure

1-acetyl-1H-cyc...

~%

2-methyl-2H-acenaphthylen-1-one Structure

2-methyl-2H-ace...

1-(triphenylphosphino)-1H-cyclobuta(de)naphthalene bromide Structure

1-(triphenylpho...

~%

2-methyl-2H-acenaphthylen-1-one Structure

2-methyl-2H-ace...

1-bromo-1H-cyclobuta[de]naphthalene Structure

1-bromo-1H-cycl...

~%

1-Naphthalenecarboxylicacid, methyl ester Structure

1-Naphthaleneca...

1H-Cyclobuta[de]naphthalene Structure

1H-Cyclobuta[de...

~%

1-Naphthalenecarboxylicacid, methyl ester Structure

1-Naphthaleneca...

(1H-cyclobuta[de]naphthalen-1-yl)lithium Structure

(1H-cyclobuta[d...

~%

1-Naphthalenecarboxylicacid, methyl ester Structure

1-Naphthaleneca...

(1H-cyclobuta[de]naphthalen-1-yl)magnesium bromide Structure

(1H-cyclobuta[d...

~%

1-Naphthalenecarboxylicacid, methyl ester Structure

1-Naphthaleneca...

1-(thiophenoxy)-1H-cyclobuta(de)naphthalene Structure

1-(thiophenoxy)...

~%

1-Naphthalenecarboxylicacid, methyl ester Structure

1-Naphthaleneca...

Methanol Structure

1H-cyclobuta(de)naphthalen-1-one Structure

1H-cyclobuta(de...

~66%

1-Naphthalenecarboxylicacid, methyl ester Structure

1-Naphthaleneca...

1-chloro-1-(thiophenoxy)-1H-cyclobuta(de)naphthalene Structure

1-chloro-1-(thi...

~%

1-Naphthalenecarboxylicacid, methyl ester Structure

1-Naphthaleneca...

1-(triphenylphosphino)-1H-cyclobuta(de)naphthalene bromide Structure

1-(triphenylpho...

~%

1-Naphthalenecarboxylicacid, methyl ester Structure

1-Naphthaleneca...

(1H-cyclobuta[de]naphthalen-1-yl)lithium Structure

(1H-cyclobuta[d...

~%

1-Isobutylnaphthalene Structure

1-Isobutylnapht...

Reductive cleavage of aryl oxazolines to benzaldehydes and s...

[Meyers, A. I.; Himmelsbach, Richard J.; Reuman, Michael Journal of Organic Chemistry, 1983 , vol. 48, # 22 p. 4053 - 4058]

Palladium-Catalyzed Cyclization of. omega.-Haloallenes. A Ne...

[Ma, Shengming; Negishi, Ei-Ichi Journal of the American Chemical Society, 1995 , vol. 117, # 23 p. 6345 - 6354]

No. 1-2902

[Brown, George R.; Foubister, Alan J. Synthesis, 1982 , # 12 p. 1036 - 1037]

Catalytic transfer hydrogenation of hydrophobic substrates b...

[Journal of Molecular Catalysis A: Chemical, , vol. 366, p. 210 - 214]

Facile reductive dehalogenation of organic halides with nick...

[Khurana, Jitender M.; Kumar, Sanjay; Nand, Bhaskara Canadian Journal of Chemistry, 2008 , vol. 86, # 11 p. 1052 - 1054]