DETAILED ACTION
Status of Application
This action is responsive to nonprovisional application filed 05/24/2023. Original claims 1-3 are currently pending and under examination herein.
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA . However, in the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for a rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
Information Disclosure Statement(s)
The information disclosure statement(s) (IDS) filed on 05/24/2023 and 09/03/2025 are in compliance with the provisions of 37 CFR 1.97, 1.98 and MPEP § 609, and therefore the information referred to therein has been considered as to the merits. Initialed copies of the IDS are included with the mailing/transmittal of this Office action.
Foreign Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Claim Rejections – 35 U.S.C. 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claims 1 and 3 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Rondan et al (Tetrahedron Letters, Vol. 25, No. 24, 2519-2522, 1984) (‘Rondan’).
Regarding Claims 1 and 3, Rondan has already described the thermal sigmatropic isomerization of 1,3-pentadiene via 1,5-hydrogen shifts as depicted in the formulation below:
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(pp. 2519-2520) In the depicted scheme, the structure at the left-hand side is seen to correspond to the Applicant’s conjugated diene compound (2) of general formula (2), where Z is a methyl group, m is 0 and n is 1, while the structure at the right-hand side corresponds to the Applicant’ conjugated compound (4) of general formula (4) where Z is as defined above, m+1=1 and n-1=0. As such, Rondan is considered to fully describe the claimed process for preparing a conjugated diene compound where a conjugated diene compound (2) of the general formula (2) is subjected to an intramolecular sigmatropic rearrangement reaction to obtain a conjugated diene compound (4) of the general formula (4).
Claims 1 and 2 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by O’Neal et al (J. of Chem. Kinetics, Vol. 11: 343-347 (1970)) (‘O’Neal’).
Regarding Claims 1 and 2, O’Neal has already described the thermal isomerization of cis-hepta-1,3-diene via a 1,5-hydrogen shift as proceeding almost stereospecifically to cis-2-trans-4-heptadiene as shown below:
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(pp. 344-347 (Tables I, II)) The cis-1,3 diene structure is seen to correspond to the Applicant’s conjugated diene compound (1) of general formula (1), where Z is a methyl group, n is 0 and m is 3, while the cis-2-trans-4 diene structure corresponds to the Applicant’ conjugated compound (3) of general formula (3) where Z is as defined above and n+1=1 and m-1=2. While O’Neal does not explicitly refer to the described thermal isomerization as a sigmatropic rearrangement reaction, the reaction depicted above clearly involves an intramolecular rearrangement and is carried out at a temperature of ~ 100oC (see p. 344, 2nd full para), this heating temperature being well within the Applicant’s preferred reaction temperature range at which the instant reaction is said to proceed (cf., Spec., [0017]). As such, O’Neal is considered to implicitly describe the claimed process comprising: subjecting to an intramolecular sigmatropic rearrangement reaction, a conjugated diene compound (1) of the general formula (1) to obtain a conjugated diene compound (3) of the general formula (3).
Conclusion
Claims 1-3 are rejected. No claims are in condition for allowance at this time.
Correspondence
Any inquiry concerning this communication should be directed to Examiner F. M. Teskin whose telephone number is (571) 272-1116. The examiner can normally be reached on Monday through Friday from 9:00 AM - 5:30 PM.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner's supervisor, Robert Jones, can be reached at (571) 270-7733. The appropriate fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) Form at https://www.uspto.gov/patents/uspto-automated- interview-request-air-form.
/FRED M TESKIN/Primary Examiner, Art Unit 1762
/FMTeskin/01-10-26