Isobenzo furan

Benzo[c]furans (isobenzofurans) are very reactive but generally unstable dienes which are prepared in situ and trapped. The in ihu-generated isobenzo-furan 33 was trapped by cycloaddition reaction with bis(methyl (S)-lactyl) ester 34 to afford [32] optically active naphthols (Equation 2.12). The cycloaddition was carried out in the presence of a catalytic amount of glacial acetic acid and represents a facile one-pot procedure to synthesize substituted naphthols. 

CONTENTS Introduction to the Series An Editor s Foreword, Albert Padwa. Preface, Randolph P. Thummel. Isobenzo-furans, Bruce Rlckborn. Dihydropyrenes Bridged [14] Annu-lenes Par Excellence. A Comparison with Other Bridged Annulenes, Richard H. Mitchell, [l.m.n.] Hericenes and Related Exocyclic Polyenes, Pierre Vogel. The Chemistry of Penta-cyclo [5.4.0.0 .0 °.0 ] Undecane (PCUD) and Related Systems, Alan P. Marchand. Cyclic Cumuienes, Richard P. Johnson. Author Index. Subject Index. 

The currently accepted name for 4 in Chemical Abstracts (CA) is isobenzo-furan the systematic name is benzo[c]furan. It should be mentioned that L. F. Fieser strongly advocated and used the spelling isobenzofurane. The numbering of the system is as shown in 4 in the older literature, numbering as in 6 has been used."... 

Several reports of the participation of azirines as hetero dienophiles have appeared, and this subject has been reviewed.Simple alkyl and aryl azirines react with cyclopentadienones to afford azepines as the ultimate products (equation 23). This type of azirine does not react with cyclopentadiene, but the benzoyl azirine shown in equation (24) does to afford an isolable Diels-Alder adduct. Azirines have also been shown to react stereoselectively in [4 + 2] fashion with tetrazines such as (64) and isobenzo-furan. 

This section is dominated by cycloadditions involving furans and isobenzo-furans. The new dienophile ethyl (diethoxyphosphinyl)propynoate is highly... 

Benzo[c]furans , Friedrichsen, W., Adv. Heterocycl. Chew., 1980, 26, 135 Isobenzo-furan , Haddadin, M. J., Heterocycles, 1978, 9, 865 Progress in the chemistry of isobenzofurans applications to the synthesis of natural products and polyaromatic hydrocarbons , Rodrigo, R., Tetrahedron, 1988, 44, 2093 Recent advanees in the chemistry of benzo[c]furans and related compounds , Friedrichsen, W., Adv. Heterocycl. Chew., 1999, 73, 1. 

As predicted from ionization potential values, the reactivity of isobenzo-furan (261) with singlet oxygen is found to be between that of furan and 1,3-diphenylisobenzofuran. ... 

The Diels-Alder addition product (50) from butadiene and 1,2-dibenzoyl-acetylene is a versatile precursor for preparation of isoindoles, isobenzo-furans, and isobenzothiophens. ... 

CA Index Name Glycine, A,A -[l,2-ethanediylbis[oxy [4-[[(2, 7 -dichloro-3, 6 -dihydroxy-3-oxospiro[isobenzo-furan-l(3i7),9 -[9i7]xanthen]-5-yl)carbonyl]amino]-2,l-phenylene]]]bis[A-(carboxymethyl)-, potassium salt (1 8) Other Names Glycine, A,A -[l,2-ethanediylbis[oxy[4-[[(2, 7 -dichloro-3, 6 -dihydroxy-3-oxospiro[isobenzofu-ran-l(3i7),9 -[9i7]xanthen]-5-yl)carbonyl]amino]-2,l-phenylene]]]bis[A-(carboxymethyl)-, octapotassium salt CG 2 Calcium Green 2... 

CA Index Name Glycine, AT-[2-(carboxymethoxy)-4-[[(2, 7 -dichloro-3, 6 -dihydroxy-3-oxospiro[isobenzo-furan-l(3H),9 -[9/7]xanthen]-5-yl)carbonyl]aniino]phe-nyl]-A-(carboxymethyl)-, potassium salt (1 5)... 

Diels-Alder cycloaddition to 1,3-dihalogenoisoindenones is reported (Scheme 54) and the preparation of polyhalogeno-isoindoles and -isobenzo-furans described (Scheme Other novel syntheses of benzopolycyclics... 

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