"Photoreduction of aliphatic and aromatic thioketals. New access to the reduction of carbonyl groups by a desulfurization chain process"

GABRIELA OKSDATH MANSILLA; ARGÜELLO, JUAN E.;; ALICIA B. PEÑÉÑORY

TETRAHEDRON LETTERS

PERGAMON-ELSEVIER SCIENCE LTD

Lugar: Amsterdam; Año: 2012

0040-4039

Aromatic and aliphatic ketones can be converted to methylene groups by desulfurization of the corresponding dithioketals in moderate to good yields. The reaction proceeds by photoinduced electron transfer from tert-BuOK in the presence of 1,4-dicyclohexadiene as hydrogen atom donor. The diene is able to trigger and keep a chain process by hydrogen transfer-proton transfer reactions. e-mail aceptacion Fecha: 14/12/12 (19:31:57 ART) De: John Wood Para: penenory@fcq.unc.edu.ar Asunto: Decision on your submission TETL-D-12-03002 Texto (5 KB) Ms. Ref. No.: TETL-D-12-03002 Title: Photoreduction of aliphatic and aromatic thioketals. New access to the reduction of carbonyl groups by a desulfurization chain process Tetrahedron Letters Dear penenory, Reviewers have now commented on your paper. You will see that they are advising that you revise your manuscript. If you are prepared to undertake the work required, I would be pleased to reconsider my decision. For your guidance, reviewers' comments are appended below. If you decide to revise the work, please submit a list of changes or a rebuttal against each point which is being raised when you submit the revised manuscript. Please submit your revision within the next 60 days, however if you are unable to do so within this timescale please let us know. When submitting your revised manuscript, please ensure that you upload the source files (e.g. Word). Uploading a PDF file at this stage will create delays should your manuscript be finally accepted for publication. If your revised submission does not include the source files, we will contact you to request them. To submit a revision, please go to http://ees.elsevier.com/tetl/ and login as an Author. Your username is: penenory@fcq.unc.edu.ar If you need to retrieve your password details, please go to: http://ees.elsevier.com/TETL/automail_query.asp For further guidelines on how to submit your revised manuscript please go to the following address: http://help.elsevier.com/app/answers/detail/p/7923/a_id/91 On your Main Menu page is a folder entitled "Submissions Needing Revision". You will find your submission record there. PLEASE NOTE: The journal would like to enrich online articles by visualising and providing details of chemical structures defined as the main chemical compounds described in Tetrahedron Letters articles. For this purpose, corresponding Mol Files can be uploaded in our online submission system. Submitted Mol Files will be available for downloading from your online article on ScienceDirect. Elsevier will generate InChI keys from the Mol Files and include them in the online article, which increase the online searchability of your article (e.g., in Google). More information can be found at http://help.elsevier.com/app/answers/detail/p/7923/a_id/661. If you wish, you can submit Mol Files along with your revised submission. Yours sincerely, John Wood Editor Tetrahedron Letters Reviewers' comments: Reviewer #1: This is a very nice manuscript that warrants publication in a highly visible format such as Tetrahedron Letters. It describes a very useful deoxygenation procedure that will be of wide interest to the organic community. The manuscript is well organized but I do have a few minor editorial suggestions. (1) column 1 page 1 line 3; insert "in" between "altogether," and "a". (2) column 1 page 1 line 6; replace "one involve" with ""include". (3) column 1 page 1 line 4 from bottom of column; insert "an" between "for" and "aromatic" and in the following line change it to read, "to methylene transformation by desulfurization of the". (4) column 1 page 2 line 8; insert "a" between "under" and "nitrogen". (5) column 1 page 2 4th line below Table 1; replace "determined" with "obtained". (6) column 2 page 2 line 2; replace "previous" with "prior". (7) column 2 page 2 line 4; replace "over" with "to the red of". (8) column 2 page 2 line 5; replace "to a solution of 7" with "relative to 7". (9) column 2 line 3 above Scheme 2; replace "ends in" with "generates". (10) column 1 page 3 line 1; 1,4-cyclohexadiene is misspelled. (11) column 1 page 3 line 7; The sentence beginning in this line is not a complete sentence. I recommend that the period be removed to read "reaction since it is well.." (12) column 1 page 3 line 9; delete "a". (13) column 1 page 3 line 16; delete "the" at the end of the line and "any" in the following line. (14) column 1 page 3 line 23; replace "in" at the end of the line with "at". (15) column 1 page 3 line 27; delete "up". (16) column 1 page 3 line 33; replace "building up" with "propagating". (17) column 1 page 4 line 5; Change to read "In conclusion, we have developed photoinduced reductive methodology to convert the carbonyl group in aromatic and aliphatic ketones to CH2 groups by desulfurization of the corresponding dithioketals." (18) reference 4 line 8; change to read "by the addition of excess ammonium nitrate and 10 mL ." (19) reference 12 last 2 lines; "303.1236 found 303.1195" rather than "303,1236 found 303,1195" ********************************************************* For further assistance, please visit our customer support site at http://help.elsevier.com/app/answers/list/p/7923. Here you can search for solutions on a range of topics, find answers to frequently asked questions and learn more about EES via interactive tutorials. You will also find our 24/7 support contact details should you need any further assistance from one of our customer support representatives.