1989
DOI: 10.1002/hlca.19890720111
|View full text |Cite
|
Sign up to set email alerts
|

Photochemistry of Thiophen‐2(5H)‐ones

Abstract: Dedicated to Prof. Dr. 0. E. Polunsky on the occasion of his 70th birthday (4.XI. 88)Mechanistic evidence for the light-induced ring opening of thiophen-2(5H)-ones 1 in alcohols affording c@-unsaturated mercapto esters 2 is presented. Regio-and stereochemical aspects of the ring closure of alkenylthio (type 3) radicals 15 and 17 to S-heterocycles 16 and 18, of 3-thiahex-5-enyl radicals 4 to (tetrahydrothien-3-yl)methyl radicals 6 and of (2,3-dihydrothien-3-yl)methyl radicals 30 (type 7, but-3-enyl radicals) to… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2

Citation Types

0
3
0

Year Published

1989
1989
2009
2009

Publication Types

Select...
5
2

Relationship

1
6

Authors

Journals

citations
Cited by 17 publications
(3 citation statements)
references
References 24 publications
0
3
0
Order By: Relevance
“…While 2(5H)-furanones exhibit a typical enone-like behaviour, giving rise to cyclic dimers, [2 + 2] cycloadducts with alkenes or photoreduced products (e.g., saturated lactones) in alcoholic solutions via triplet state [16,18], the unsaturated thiolactones undergo ring opening to a,b-unsaturated mercapto esters via singlet state. On the other hand, it has also been shown that, like furanones, thiophenones can also undergo [2 + 2] photocycloadditions with alkenes in cyclohexane solution [11]. Interestingly, in all above mentioned studies, furanones and thiophenones were involved in cross-reactions with the solvent, whereas the photochemical behaviour of the isolated compounds (either in gaseous phase or in inert matrices), as far as we know, was not reported hitherto.…”
Section: Introductionmentioning
confidence: 93%
See 1 more Smart Citation
“…While 2(5H)-furanones exhibit a typical enone-like behaviour, giving rise to cyclic dimers, [2 + 2] cycloadducts with alkenes or photoreduced products (e.g., saturated lactones) in alcoholic solutions via triplet state [16,18], the unsaturated thiolactones undergo ring opening to a,b-unsaturated mercapto esters via singlet state. On the other hand, it has also been shown that, like furanones, thiophenones can also undergo [2 + 2] photocycloadditions with alkenes in cyclohexane solution [11]. Interestingly, in all above mentioned studies, furanones and thiophenones were involved in cross-reactions with the solvent, whereas the photochemical behaviour of the isolated compounds (either in gaseous phase or in inert matrices), as far as we know, was not reported hitherto.…”
Section: Introductionmentioning
confidence: 93%
“…Margaretha and co-workers [6][7][8][9][10][11][12][13][14][15][16][17] reported that upon irradiation 2(5H)-thiophenones behave quite differently from the corresponding oxygen-based heterocycles. While 2(5H)-furanones exhibit a typical enone-like behaviour, giving rise to cyclic dimers, [2 + 2] cycloadducts with alkenes or photoreduced products (e.g., saturated lactones) in alcoholic solutions via triplet state [16,18], the unsaturated thiolactones undergo ring opening to a,b-unsaturated mercapto esters via singlet state.…”
Section: Introductionmentioning
confidence: 99%
“…We had shown that both 3(2H)-and 2(5H)-furanones l a and 2a and 3(2H)-thiophenone l b exhibit photochemistry typical for cyclopent-2-enone itself and that 2(5H)-thiophenones, e.g. 2b, behave differently in undergoing light-induced ring-opening reactions in hydroylic solvents [6] [7]. Finally, while lH-pyrro1-3(2H)-one l c is photoinert [8], the corresponding N-(ethoxycarbonyl) derivative Id again exhibits typical enone behavior [9].…”
mentioning
confidence: 99%